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A SURVEY OF COMPOUNDS FROM THE

ANTIRADIATION DRUG DEVELOPMENT

PROGRAM OF THE U.S. ARMY MEDICAL

RESEARCH AND DEVELOPMENT COMMAND

T.R. Sweeney

September 1979 9 .

WALTER REED ARMY INSTITUTE OF RESEARCH

WASHINGTON, D.C.

Approved for Public Release;Distribution Unlimited

DEDICATION

Thls survey is dedicated to Dr. David P. Jacobusand Dr. William E. Rothe whose warm encouragemenafacilitated its writing and expedited its completion.

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CONTENTS

page

Preface iii

List of Tables iv

Introduction 1

Methods 9

Introduction to the Survey 11

The Survey; Summary of Antiradiation Activity 15

List of balts and Other Forms of Compounds Tested 651

References Cited in the Survey 655

Structure-activity Relationships 671

Walter Reed Number Index 773

PREFACE

In the present survey of the Antiradiation Drug Development Program of the

U.S. Army Medical Research and Development Command, an attempt has been made to

assemble in one place all of the compounds that were synthesized along with the associated

mouse test results and offer an interpretation of the biological data vLs a vis the structures of

the compounds. This edited body of data has been organized for quick and easy reference

both for those working in the field and for the casual reader. it was not the intention to re-

port on all of the work that was done in the Program. The arbitrary decision was made not to

extend the survey to include results of indepth studies that were carried out on a number of

the more interesting compounds; such studies could include, for example, determination of a

dose reduction factor, duration of action and mechanism of the chemical antagonism of anti-

radiation action. Results on the testing of selected compounds in large animals have also been

omitted. Finally, results of the various preclinical pharmacology studies that were carried out

to support the requests for exemptions to conduct clinical studies of drug tolerance, as well

as the results of the tolerance studies, have also been omitted.

There are two principal parts of this survey. One, which may be considered the survey

proper, is a large table simply entitled Survey. In it is summarized the results of the testing of

all of the target compounds synthesized in the program as well as a small number of related

gift compounds that seemed to be of sufficient interest to include. The other principal part,

following the survey proper, is a discussion of structure-activity relationships among selected

series of compounds along with 47 tables of associated data. The latter tables contain only a

small portion of the compounds that are included in the Survey.

Many people contributed to the success of the program over its active years, not only

those associated with it at the Walter Reed Army Institute of Research, but also those at the

Headquarters, U.S. Army Medical Research and Development Command as well as those

associated with the many contractors. Special mention must be made of Dr. David P. Jacobus

whose initiative and izpiration provided the impetus for the program and who served as its

technical director during its most active years. Succeeding Dr. Jacobus was Dr. William E.

Rothe who directed the technical program until its termination in 1973.

The author is indebted to June A. Page, Larry J. Hooks, Sandra M. Simpson and

Ruby N. Boyd for technical assistance in the collection of data for this survey and to

Marie M. Grenan for assistance in the collection of biological data and consultation on their

interpretation. Special thanks and acknowledgement is made to David P. Jacobus for consul-

tation and suggestions for valuable inclusions in the survey.

LIST OF TABLES

Table No. PAPe

1* 3-42-Mercaptoethylamino)propiciamide and Derivatives. 691Effect of Varying the Thiol-blocking Group.

2. 2-43-Aminopropylamino)ethanethiol and Derivatives. 692Effea~ of Varying the Thiol-blocking Group.

3. n-Decylamlinoethaethiol and Derivatives. 693Effect of Varying the Thiol-blocking Group.

4. 2-Aminoalkylthiols. 694

5. 2-Aminoalkyithiosulfuric Acids. 695

6. 2-Azninoalkylphosphorothioates. 696

7. 2-Mercaptoalkylamines. 697

8. 2-Thiosulfatoalkylamines. 698

9. 2-Aminoethanethiols. Effect of Functionahized Substituents. 699

10. 2-Aminoethylphosphorothioates. Effect of Functionalized 700Substituents.

)I. Alkylaminoethanethiols and -thiosulfates. 701

12. Branched- alkybaminoethanethiols and -tbiomhf uric acids. 702

13. Phenalkylniminoethanethiols. 704

14. Phenalkybaininoethanethiomzlfuric Acids. 705

15. Hydroxyallcylaminoethanethiols. 707

16. Hydroxyalkylaminoethanethiosulfuric Acids. 709

17. Hydroxyalkylamninoethylphosphorothioates. 71.0

18. Hydroxyalkylazniinoethyldisulfides- 711

19. Alkoxyalkylaminoethanethiols and -thiosulfuric Acids. 712

20. Cycloalkyloxyaminoethanethiosulfurfic Acids. 714

21. Phenoxyalkylaminoethanethiols. 715

22. Phenoxyalkylaminoethnnethlosfuhfuc Acids.71

23. Phenoxyalkylanmlnoethyldlsulides. 719

24. 3-(Phenoxyalkyl)thiazolldines. 720

25. Cycloalkylalkylaxniinoethanethiosulfuric Acids. 721

26. Cycloalkylalkyhaminoethanetohol. 726

27. Cycloalkylalkylaminoet~hyldisulfkles. 728

28. Cycloalkylakylaminoethylphosphorothioates. 729

iv

Table No. Page

29. 2.Pyridyloxyalkylaminoethanethiosulfuric Acids. 730

30. 2-Quinolyloxyalkylaminoethanethiosulfuric Acids. 732

31. 2-Pyridyloxyalkylaminoethanethiols. 734

32. Substituted 2-[(3-thiazolkdinylalkyl)oxy ] pyridines. 735

33. Substituted 2-4 (3-thiazolidinylalkyl)oxyJ quinolines. 737

34. Substituted 2-[(3-thiazolidinylalkyl)thio) pyridines. 738

35. 3-1(Alkylthio)alkylJ thiazolidines. 740

36. Aminoalkylaminoethanethiols. 742

37. Aminoalkylamninoethylphosphorothioates. 747

38. Aminoalkylaminopropanethiols. 752

39. Aminoalkylaminopropylphosphorothioates. 753

40. Parent acetamidine Derivatives. 754

41. Alkyl-o-amidinium Thiosulfates. 755

42. Arylalkyl-a-amidinium Thiosulfates. 757

43. Phenoxy- and phenylthioalkyl-a-amidinium Thiosulfates. 759

44. Cycloalkyl-a-amidinium Thiosulfates. 760

45. Cycloalkyl-a-amidinium Disulfides. 764

46. EffP•; of Chain Length on Activity of Mercaptoamidines 768and Derivatives.

47. No-nitrogen Antiradiation Compounds. 769

48. Compounds Effecting at Least 50% Survival at a Dose of One Fourth 770of the Highest Dose Tested, Either I.P. or P.O. and the Table in whichthe Data Appear.

49. Compounds Effecting at Least 50% Survival at a Dose < 15 mg/kg, Either i.P. 771or P.O. awd the Table in which the Data Appear.

V

INTRODUCTION

In the spring of 1959 the U.S. Army Medical Research and Development Command

initiated a program of drug development for chemoprophylactic agents that could protect

troops against ionizing radiation. The technical part of the program was the responsibility of

the Walter Reed Army Institute of Research and was initiated under the technical direction

of Dr. David P. Jacobus. The quantitative biological data that were generated in the program

were originally classified but the program was declassified in 1965.

Although there was a parall'l in-house effort, the bulk of the chemical synthesis was

carried out through research contracts with industry, research institutes and universities. Most

of the biological testing and pharmacology was done in-house although it eventually became

necessary to supplement the in-house efforts with appropriate contracts. The large number of

chemicals and the laige volume of chemical and biological data necessitated the development

of computerized methods of handling (1,2,3,4).

The program was planned and organized in such a way that all of the elements neces-

sary for modem drug development were phased in at appropriate times. Thus while rational

synthesis and primary testing were emphasized at the outset of the program, there followed

in timely succession the program elements of advanced screening in large animals, indepth

studies on compounds of interest, preclinical pharmacv!ogical studies, formulation investiga-

tions, preparation and appropriate review of the necessary documentation for human toler-

ance studies, and, finally, human tolerance studies. A total of about 4400 target compounds

were synthesized in the program. Five formal requests for new drug exemptions (INDs) were

prepared and human tolerance studies were conducted on three of these.

Prior to the advent of the Army program there had accrued a considerable body of

data that indicated the feasibility and desirability of such a study. The Atomic Energy Com-

mission had evaluated the mechanism of action of ionizing radiation, characterized the syn-

dromes associated with radiation mortality and sponsored studies on the mechanism of

action of thiol derivatives in various rodents, microorganisms and in vitro cultures. Patt in

1949 (5) had shown that cysteine, administered before irradiation with x-rays, brought about

a substantial reduction of radiation injury in rats. Two years later it was demonstrated

that the cysteine analog, cysteamine (MEA), protected mice if administered before

x-irradiation (6). Both of these compounds contain unsubstituted amino and thiol groups. In

1955 it was reported that S-2-amino-ethylisothiuronium bromide hydrobromide (AET) had

good antiradiation activity (7) and, finally, in 1959 the good radioprotective properties of

i , I I II II I I1

2-aminoethylthiosulfuric (the Bunte salt of MEA) were reported (8). Also, by the time the

program began, about 1500 compounds had been tested elsewhere, mainly at the U.S. Air

Force Radiation Laboratory in Chicago (9). The best compounds from this group were those

having a potential thiol group separated by 2 or 3 carbons from a basic nitrogen function.

In this same pre-program period, Eldjarn and Pihl (10) had provided a possible theoreti-

cal basis for the mechanism of action of the thiol compounds against radiation-induced radi-

cals (indirect action) and against the radiation itself. They suggested that mixed disulfide

formation of the protective thiol with essential thiols of the target molecule shields the latter

by providing a non-lethal target for radiation-induced radicals and a source of electrons (the

disulfide bond) for repair of an electron deficiency elsewhere in the molecule, both processes

leading to a regeneration of the original essential thiol.

Many studies had been conducted on methods of modifying the response to sub-

lethal radiation as opposed to fully lethal radiation. Survival against sub4ethal radiation could

be improved by modification of host defense. Thus, non-physiological materials can stimulate

the reticuloendothelial system to produce leucocytes or enhance the defense against bacterial

invasion (antibiotics) and can offer very significant protection against mid-lethal radiation.

Partial shielding will also offer protection. In general, where appropriate experiments have

been conducted, such manipulations work in concert with the aminothiols, i.e., reduction of

lethal radiation to mid-lethal by administration of an aminothiol would provide an animal

that could be effectively treated with antibiotics. On the other hand, these host procedures

were relatively ineffective in animals exposed to fully lethal radiation. Because the objective

of the program was to develop antiradiation drugs rather than modifying host defense, almost

all of the radiation experiments and test procedures were conducted at fully lethal radiation.

As pointed out in the description of the biological methods, none of the 44,000 mice used as

controls for the approximately 4400 compounds tested survived and none showed early

deaths.

The pivotal decision to initiate the Army Program was made after Jacobus and

Dacquisto (9) found that an intravenous administration of a mixture of compounds contain-

ing at least two mercaptans, a methemoglobin-producing agent and a cytochrome inhibitor

could protect dogs exposed to approximately twice a lethal dose of radiation. The protected

dogs received no post-exposure care and maintained white counts sufficient to offer protec-

tion against disease. These experiments raised the possibility that such protective activity

could be extended to higher animals.

The studies initiated by Patt and continued by others demonstrated that the amino-

thiols had the ability to reduce irradiation injury by a factor of approximately 2. That is to

2

say, the apparent dose of radiation would appear to be half of what the animal actually re-

ceived. By a judicious selection of the dose, it was then possible to demonstrate that an ani-

mal receiving sufficient radiation to cause the CNS death syndrome would have the apparent

dose of radiation cut in half so that the fatal syndrome would then be the GI syndrome.

Likewise, the GI syndrome could be reduced to the bone marrow syndrome and the bone

marrow syndrome could be converted to survival. These dose reductions in mice were subse-

quently repeated in the Army program using both monkeys and dogs. In the Army program,

therefore, it was considered that any compound effective against lethal radiation would offer

a comparable dose reduction factor for a super4ethal radiation. Dose reduction factors as

conventionally determined in radiobiology were very rarely studied in the Army program.

However, the reader may obtain an approximation of the magnitude of the dose reduction by

noticing that any compound that received an antiradiation rating of "+", indicating at least

50% survival at the dose tested reduces the apparent dose of radiation from the LD100 of

800r to at least the LD5 0 of 600r. Therefore at the dose tested the compound would have a

dose reduction factor (DRF) of at least 1.3 (800/500). Many of the compounds tested

allowed 100% survival at 800r. Since the LD 10 of radiation for mice in the absence of drug

was approximately 450r the DRF for compounds allowing 100% survival was at least 1.8

(800/450). These relationships can be appreciated from an examination of the following data

showing actual dose reduction factors determined for WR-2721 [H 2N(CH 2 )3NHCH2CH2

SPO3 H2 ] and percent survival of WR-2721-treated mice subjected to otherwise let.iAl

radiation. The compound was administered 15 minutes pre-irradiation, IP, for both sets of

data.

Mortality Data on WR-2721-Treated MiceDose Jackson Lab Data' Survey Data

(mg/kg) (DRF) %Survival Rating3

75 n.d. 2 80 +150 1.81 100 +,+200 2.18 n.d.250 2.27 n.d.300 n.d. 100350 2.42 n.d.500 2.71 n.h.600 n.d. 100

1The Jackson Laboratory, Final Report 1 August 1968 - 31 July 1969,Contract No. DA-49-193-MD-2289.2 n.d. = not determined.

3The rating is that used in the Survey proper and explain -d in the in-troduction to the Survey. Only a rating of "+,+,+,+" for a dose of600 mg/kg, which would include the lower doses, would appear in hieSurvey and would indicate that a dose level of 1/8th of 600 mg/kg gaveat least 50% survival.

3

The background described established the setting for the program. Aminoalkylthiols,

actual or potential, were considered to be the only compounds offering "true" radioprotec-

tion •,nd even for these, there existed the possibility that their mechanism of action could be

through production of anoxia. It was not the objective of the program to obtain compounds

of this class with DRFs greater than 2-3 since it was felt that they had only one mechanism of

action and might have a DRF limit of 2-3. Rather it was to obtain a compound that was

capable of conferring significant protection at doses considerably below the highest tolerated

level such as was required by the original aminoalkylthiols. In other words, a compound with

a larger factor of safety (therapeutic index) was desired. From the practical standpoint, a

small effective dose, comparable in weight with those employed in conventional therapy, and

having a low incidence of side effects was desired. Finally, the ideal drug should be effective

by oral administration.

Toward these ends the primary test was designed to measure two parameters precisely,

viz., the effectiveness of a compound at the highest tolerated dose (semiquantitative DRF)

and the ability of the compound to confer protection when administered at less than this

dose. Norrnaiy, only one test of a compound was made if the compound exhibited no

activity in a valid experiment as determined by the response of the control animals. When a

compound exhivited interesting activity, the activity was confirmed, the compound was

reteeted at lower doses and, in addition, usually tested by oral administration. The very best

compounds were ultimately tested in dogs and/or monkeys although formal dose reduction

studies wete not conducted.

As mentioned earlier, the main thrust of the rational synthesis effort in the program

A'as directed toward aminoalkylthiols and derivatives. Adherence to the thiol-blocking

concept, discusst;J elsewhere in this survey, dictated the synthesis of compounds with several

thiol-blocking groups for each parent compound synthesized. In retrospect, this was a sound

approach but it required a substantial portion of the total synthe3is effort and to scme extent

limited the number and variety of amine-function derivatives that could be synthesized. By

exploring a large variety of thiol-blocking groups, the synthesis program can be credited with

firmly establishing the worth and utility of a select few and, in addition, obtaining a good

appraisal of the worth of a variety of classes of moieties attached to the amino function. ThN,

large number of chemical publications resulting from the synthetic effort attests to the

contribution the program made to the chemistry of aminothiols.

It was realized that it would be desirable to uncover new c'asses of active compounds.

,*oward this end screening of selected compounds outside of the aminoalkylthiol type was

carried on but no new classes emerged, even though somewhat over 1500 were tested; the

bulk of this random screening was carried out by the U.S. Air Force Radiation Laboratory

with support from the U.S. Army Medical Research and Development Command for the last

few years. Late intermediates in certain syntheses were also sometimes tested. Combinations

of what were thought to be significant groupings were also tried. Thus, the sodium sulfinate

group, -SO2Na, conferred special antiradiation properties on the [-S(CH 2)4SO2NaJ moiety

compared to the unsubstituted moiety [S(CH2 )3CH31 when used as a thiol-blocking group.

Combining this moiety in the form of a trisulfide (WR 168,643, Table 47) yielded a highly

active antiradiation compound that was atypical in that the molecule contained no nitrogen.

The theoretical significance and potential utility of this finding have yet to be explored.

Other "no-nitrogen" compounds are also active (Table 47). This class of compounds deserves

the attention of future investigators. Other classes that have probably not been adequately

explored are the amidine and aminoalkylamino derivatives.The program was originally designed to solve what was believed to be a relatively

straightforward problem in medicinal chemistry, i.e., to explore in a logical manner the limits

of the chemical lead, to test the best compounds resulting from the exploration in higherspecies and, after appropriate safety studies, to test the best compounds in man. As it turned

out, this simple medicinal chemistry format was not of sufficient sophistication to allow the

unequivocal selection of a radioprotective compound with enough of a safety margin to be

attractive for full development. The difficulty lay in the fact that neither antiradiation action

nor toxicity necessarily progressed in a simple way with logical structural variations but could

be highly specific. This finding was more surprising in view of the simplicity of the original

lead. Two examples can illustrate the problem. In the simple aikylaminoethylthiosulfuric

acids there are three separate peaks of activity as the alkyl chain is lengthened and similarlytwo peaks of activity in the corresponding thiol series. The second example is furnished by

the aminoalkylamnnoethyl derivatives where the active and adjacent inactive compounds of

the ;eries were studied for a toxic side effect, viz., alpha adrenergic blockading activity.Highly specific and reversible alpha adrenergic blockade of vascular smooth muscle, but not

of intestinal smooth muscle, was dependent upon the number of methylene groups between

the amine functions. Parenthetically, it may be mentioned that two of these highly selective

alpha adrenergic blocking compounds were also shown to repress and reverse induced hemor-

rhagic shock in three species of animals aid to prevent the deleterious hemodynamic effects

of otherwise lethal doses of endotoxin; these compounds, 5-amino-pentylaminoethyl-

phosphorothioic acid, WR-2823, and its symmetrical disulfide, WR 149,024, are presently

being developed for use in clinical emergencies. The adrenergic selectivity of these thiol

5

derivatives is to be contrasted with a non-selective alpha adrenergic blockading activity of the

one-armed nitrogen mustards now used in clinical practice. These alpha blockading com-

pounds demonstrated that simple thiols containing equally simple constituents would interact

with some but not all physiological thiols and that these interactions could be controlled by

relatively distant but simple structural modifications. Thus the program discovered and was at

the same time bedeviled by the different physiological effectiveness of these structurally

similar compounds although, in a sense, they were designed with the expectation that they

would interchange reversibly with the physiological thiols of the active sites or with disulfide

bonds. The problem might have been anticipated from the mechanism of action studies of

Eldjam and Pihl (10). Every series that was ttudied for phenomena other than antiradiation

activity (histamine release and hypotension, cardiotoxicit•i, hypertension, convulsions)

suggested the compounds did have specificity in ways that were not hnticipated. Although

pharmacological speciIcities did not necessarily correlate with radioprotection, their explora-

tion will be necessary to guide any future development of a compound with appropriate

physiological toleranc'.;. Sulfhydryl-dependent functions are of great physiologic importance

and the compounds in this program may offer the beginning of a unique approach to selective

modification of some of these functions.

With the exceptions noted earlier, this report summarizes the program through 1973

when it was terminated. The most active compounds were geiherally effective by intraperito-

real administration at a quarter of the highest tolerated dote and, on a weight basis, in the

5-10 mg/kg range. This range is still at least an order of magnitude away from doses employed

in conventicnal therepy but, in turn, is an order of magnitude improvement over the doses

required at the time the program started. Most of the compounds were markedly less effec-

tive with oral administration and even the most active orally in the mouse were inactive orally

in the monkey possibly because of poor absorption. Studies to surmount these difficulties,

either by effective formulation or structure design, are needed. For easy reference to com-

pounds that may provide promising areas for future research two special tables are provided:

those compounds that were effective (a rating of -) when administered at one quarter of the

highest tested dose are listed in Table 48 and those that were effective at 15 mg/kg or below

are listed in Table 49.

6

1. A. Feldman, D.B. Holland and D.P. Jacobus, J. Chem. Doc. 3,187 (1963).

2. D.B. Holland, D.P. Jacobus, A. Feldman and B.R. Moberly, Control Eng. I, 60(1964).

3. D.P. Jacobus, D.E. Davidson, A.P. Feldman and J.A. Schafer, J. Chem. Doc. 10, 135(1970).

4. EM. Eckerman, J.F. Waters, R.O. Pick and JA. Schafer, J. Chem. Doc. 12 38 (1972).

5. H.M. Patt, E.P. Tyree, R.L. Straube and D.E. Smith, Science 110 212 (1949).

6. Z.M. Bacq, A. Herve, J. Lecompte, P. Fisher, J. Blavier, G. Dechamps, H. LeBilan andP. Rayet, Arch. Intern. Physiol. 59,442 (1951).

7. D.G. Doherty and W.T. Burnett, Jr., Proc. Soc. Exp. Biol. Med. 89, 312 (1955).

8. B. Sorbo, Arch. Biochem. Biophys. 98, 342 (1962).

9. D.P. Jacobus and M.P. Dacquisto, Mil. Med. 126, 698 (1961).

10. L. Eldjarn and A. Pihl, J. Biol. Chem. 225,499 (1957).

7

METHODS

Cornpounds

The synthetic procedures ior all of the compounds that were synthesized under Army

support are given in the respective references in the Survey.

Evaluation of Compounds

An adequate description of the test system was usually not included in the chmnistry

pu\ ations. For this reason it is included in this survey.

Female mice of the Walter Reed Bagt Swiss or Inbred Charles River (ICR) strains, 5-6

weeks old and weighing 21-25g, were ratidomly assigned to treatment groups. An estimation

of the toxicity of each compound to be tested for antiradiation activity, i.e., a determination

of the approximate LD 5 0 (ALD50), was obtained in separate experiments prior to irradia-

tion. Toxicity estimations were based upon anirmial survival over a ten-day observation period

following intraperitoneal or oral administration of each agent in graded doses using 10 mice

at each dose level. Adverse symptomatology was noted and, in addition, each mouse was

subjected to a post mortem examination. The highest dose of each compound administered

for antiradiation testing was about tw.vo thirds of the ALD 50 unless a lower dose was indi-

cated by adverse symptomatology or pathologic changes; the selected doses of each com-

pound were administered 15-30 minutes before exposure to lethal whole body irradiatioin. -

Compound formulations were freshly prepared for administration prior to use. The

compounds were, depending on their solubility, either dissolved in physiological saline solu-

tion or were homogenized in a glass tissue grinder in a suspending medium of physiological

saline , ,lution containing 0.2% methyl cellulose (4000 centipoise) cnd 0.4% Tween-80. The

suspensions were exposed to an ultrasonic apparatus for approximately two minutes to in-

sure uniform particle size. The pH range of the solutions or suspensions was adjusted to 5-8,

if necessary, provided the compound was stable at the adjusted pH.

Irradiation of the mice was performed utilizing either of two sources: 300 KCP GE

Maxitron Unit, with radiation factors of 20 ma. HVL 2 mm Cu, TDS 85 cm, dose rate in air

45 r/min or a specially designed Co-60 irradiator, which contained 1200 curies of Co-60, half

above and half below the radiation chamber, with a dose rate rangt from 1 OOr - 50r/min over

a fivy year period.

Forty mice were exposed in a perforated Lucite dish 20 inches in diameter which ro-

tated continuously during exposure. Control mice injected with only the vehicle used for the

particular drug evaluation were irradiated simultaneously with each treated group and there-

after housed jointly eight to a cage.

The mice were given food and water ad libitum. The drinking water contained

10-15 ppm of chlorine to suppress the growth of Pseudomonas aeruglnosa. The principles

of laboratory animal care as promulgated by the National So,.iety for Medical Research were

observed.

"" Mortality was tabulated for a 30-day period for each individual animal and all data

computerized. Under our conditions, approximately 800r x-ray and I OOOr Co-60 gamma ir-

radiation were equally lethal (LD-100 3 0 ), all control animals dying between the tenth and

twenty-fint days following exposure. CIs p

10

INTRODUCIION TO THE SURVEY

Molecular Formula

Compounds are listed in the table in molecular formula order, the molecular formulabeing recorded in accoriance with the system used in Chemical Abstracts.

Alkali and alkaline ath metal salts of acids are recorded as tht molecular formula of

the ftee acid; other metal salts and chelates are recorded as such, all elements being includedin the molecular formula. Ammonium and amine salts of acids are also recorded as the freeacids. Acid salts of amines, such as hydrochlorides, are recorded as the free amine. Quater-

nary, sulfonium and analogous salts are recorded as such.The molecular formula of a polymer is recorded as that of the monomer and a copoly-

mer as the combination of the monomers on a I : I basis, thus (-CH 2CH-)n would be found

6COCH 3

as C4 H6 OS and (-CH 2-CH-)n - (-CH 2 -CH-)n would be found as C10H1 8N2 0 2 S.

CONH2 6 N(C2H5 )2The Walter Reed Number Index will facilitate the finding of a compound in the table

if only the Walter Reed number (WR number) is known.

WR Number

The WR (Walter Reed) number is an accession number that is assigned to each uniquestructure received. Compounds with identical molecular formulas are entered in ascendingWR number.

Structure and Confizuration

When possible to do so without sacrificing clarity, structures have been drawn linearly,using appropriate parentheses and brackets, in order to save space. Rings have been drawn

and aromatic rings are represented with appropriate double bonds.Compounds containing asymmetric center, are designated by the letters D, L, or DL

when the stereoisomer is known; unless specifically so designated it should be assumed thatthe compound is the racemic mixture. The configuration of sugar derivatives is designatedeither by Haworth projection formulas or descriptor terms such as gluco, gslacto, etc. Cisand teens isomers are designated by the appropriate descriptor term.

Although many of the compounds exist as Inner salts, e.g., the aminoalkylthiosdfuricacids, they are recorded as non-ionic. The quaternary and sulfonium salts, however, are re-corded as a cation and anion.

11

Salt Form

The numbers in the Salt Form column refer to the corresponding numbers in the table

entitled Salts and Other Forms of Compounds Tested; hydrates and solvents are induded in

this table. The salt form denotes the form in which the compound was received and tested.

Antiradiation Activity

Data for both intraperitoneal (I.P.) and oral (P.O.) administration of compounds are

given when available. The efficacy of a compound is measured by its ability to protect mice

against a dose of ionizing radiation that would otherwise be lethal, protection being defined

as a 30 day survival. The gradinp., protective effect against fully lethal radiation is ex-

pressed according to the followiEr .;,jtrary scale: 0 to 19% survival = 0; 20-49% survival =

50-100% survival = +. The pre-Ision of the test system does not warrant a narrower interpre-

tation of the data. Occasionally compounds were tested using a sublethal dose of radiation in

which case protection was defined as a st-tistically significant increase in the number of

treated mice that survived versus the controls. The rating of such a statistically significant in-

crease is indicated by the letter "S". If there is no significant difference when tested at a sub-

lethal radiation the rating given is simply zero, no reference being made to the degree of

protection or to the fact that the dose of radiation was sublethal.

After the highest dose of a compound was selected for antiradiation testing, as ex-

plained under Methods, lower doses were arbitrarily set by successively reducing each dose by

one half. A rating, as explained above, is given for each dose tested but only the highest dose

is recorded in the Survey and other tables since the lower doses that were used are obvious.

Very early deaths, I.e., at four days or fewer, are attributed to toxicity of the compound, the

effect becoming apparent in the presence of the added stress of radiation. Such a toxic effect

is indicated by a (T) following the rating symbol. This combined toxic effect is occasionally

manifested in the form of survivors at fractional drug doses but none at the top dose. For

this reason the data presented always include a rating for one dose below the lowest dose that

caused early deaths. The rating system can be illustrated using the data fcor compound

WR-176,241, H2 N(CH2 OH) 2CH2SPO3H 2 , which shows good activity. At a dose of

1000 mg/kg, intraperitoneally, the rating is given as +(T),+,+,± which means that 50% or

more of the mice survived with a drug dose of 1000 mg/kg but there were some early deaths;

50% or more of the mice survived following doses of 500 mg/kg or 250 mg/kg and between

20% and 49% of the mice survived after a dose of 125 mg/kg. Since no rating was given for

a dose below 125 mg/kg it can be assumed that the compound was not tested at that level.

12

When tested orally at 1000 mg/kg the indicated rating is 0,± which means that there were

fewer than 20% survivors at a dose of 1000 mg/kg, whereas, there were between 20% and

49% survivors at a dose of 500 mg/kg. While no early deaths were noted, the increase in the

number of survivors at the lower dose, compared to the higher, probably reflects the effect

of the combined insults.

Although expressing the dose of compound on a molar rather than a milligram basis

would often allow a more refined comparison of activity, the decision was made to retain the

milligram basis because the drug doses were selected on a milligram basis and the actual size

of a dose is better appreciated and compared from the practical standpoint. The doses of the

compounds tested, as recorded in the table, refer to the free base or non-salt form of the

compound.

References

The last column in the table gives a reference to the synthesis of the compound, if

available, provided the compound was synthesized as part of the Army's Antiradiation Drug

Development Program. Primary references, publications and patents, are given if possible. If

the synthesis of the compound has not been published, a report is referenced. Generally a re-

port will also be referenced, if the compound is mentioned only in a patent. If the synthetic

procedure is not available the source or submitter of the compound is referenced. No attempt

has been made to obtain from the open literature the procedures for the synthesis of gift

compounds; rather, the source or submitter is acknowledged.

13

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SALTS AND OTHER FORMS OF CO~WPOUNDS TEVMP

i. Hydnwcdiordd

2. Dihydrochloride

3. Trihycirochioride

4. Tetrahydrochiouide

5. Dodecahydrochloride

6. Hydrobromtide

7. Dihydrohydrobromide

8. Tuihydrobromide

9. Tetmhydfobromide

10. Hydrolodide

11. Dihydroiodide

12. Tctmhydroiodidc

13. Hexahydrosulfide

14. Phosphate

15. Dlphosphate

16. Triphosphate

17. Tetraphosphate

18. Thiophosphate

19. 0,0-Diethyithiophosphate

20. OO-Dhnethyiydithiophosphate

2 1. O,-Diethyldlthiophosphate

22. Diphenylthiophosphlnate

23. Diphenyldithiophosphinate

24. Sulfate

25. Disulfate

26. Thiosulfate

27. p-Toluenesuffonate

28. Di-p-olucnesulfonate

29. Tri-p-tohaencsulfonate

30. Tetra-p-toluenmsufonate

31. Methanesulfonate

32. Dimnethanesuhionate

33. Formiate

651

SALTS AND OTHER FORMS OF COMPOUNDS TESTED (Continued)

34. Acetate

35. Trichloracetate

36. Mal•ate

37. Funarate

38. Succ•mate

39. Tartrate

40. Benzoate

41. Hemihydrate

42. Hydrate

43. Saquihydrate

44. Dihydrate

45. Trihydrate

46. Tetrhydrate47. Pentahydrate

48. Hexahydrate

49. HeptahydrateSO. Octahydrate

51. Nonahydrate

52. Calcium Salt53. Lithium Salt54. Dtlithium Salt

55. Potassium Salt

56. Dipotauium Salt

57. Sodium Salt

58. Disodium Salt59. Trbsodium Salt

60. Ammonium Salt61. Diammonium Salt62. Trianmonium Salt63. Methylammonium Salt64. n-Propylammontum Salt

65. Octamnonium Salt66. Cyclohexylammonium Salt

652

SALTS AND OTHER FORMS OF COMPOUNDS TESTED (Continued)

67. Pyridiniun Salt

68. 2-Aminopyridiniwn Salt

69. 1-Methyl-2-knino-l ,2-dihydropyrimidmiuin Salt

70. 1 -Methyl4imnino-l ,4-dihydropynidinium Salt

71. I-Methyl-2-kimino-l ,2-dihydropyridinum Salt

72. Piperidiniwn Salt

73. Pipcraziniwn Salt74. Dipiperuinium Salt

75. Guanidinium Salt

76. Hydrazinium Salt

77. Methanolate

78. Ethanolate

79. Propanolate

80. Isopropanolate

81. Tetrafluoroborate

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115. F.I. Carroll, J.D. White and M.E. Wall, J. Org. Chem., 28, 1240 (1963).

116. Southern Research Institute, Annual Progress Report No. 8679-11 12-VI, July 1,1966-June 30, 1967, Contract No. DA-49-193-MD-2028.

117. T.P. Johnston and C.R. Stringfellow, J. Med. Chem., 9, 921 (1966).

118. D.C. Dittmer, O.B. Ramsay and R.E. Spalding, J. Org. Chem., 28 1273 (1963).

119. University of Illinois, Ph.D. Dissertation, T.T. Conway, 1967, Contract No. DA-49-193-MD-2047.

20. Eb-s Research and Engineering Company, Annual Technical Report No. 9, Juiy 1,1972-August 31, 1973, Contract No. DA-49-143-MD-2608.

12l. onsanto, Research Corporation, Sixth Annual Progress Report, April 1, 1965-March 31, 1966, Contract No. DA-49-193-MD-2109.

122. Southern Research Institute, Annual Progress Report No. A.098-2133-II1, 1971-! 972, Contract No. DADA 17-69-C-9033.

123. Soutncrn Research lnro+"ute, Annual Prceress Report No. 7468-1112-IV, July 1,l•5 4-June 30, 1965, Contract No. DA-49-193-MD-2028.

I. 4. R.D. Westland, J.L. Holmes, B. Green, and J.R. Dice, J. Med. Chem., I 824 (1968).

125. Sibm.tted by Yale University, Contract No. DA-49-193-MD-2106.

126. Southern Research Institute, Annual Progress Report No. SORI-KMA-73-113 (1972-1973) Contract No. DADA 17-69-C-9033.

127. G.C. Curtif and B. Buchner, U.S. Patent No. 3,286,002, November 15, 1966.Assigned to Continental Oil Co.

660

128. University of New Mexico, Final Report, March 16, 1960-March 15, 1962, ContractNo. DA-49-193-MD-2105.

129. Submitted by Massachusetts College of Pharmacy, Contract No. DA-49-193-

MD-2029.

130. G.W. Stacy, B.F. Barnett and P.L. Strong, J. Org. Chem., 30, 592 (1965).

131. E. Canpaigne and M.C. Wani, J. Org. Chem., 29, 1715 (1964).

132. Midwest Research Institute, Annual Progress Report No. 3, July 1, 1963-October 31,1964, Contract No. DA-49-193-MD-2174.

133. C.G. Overberger, H. Ringsdorf and N. Weinsenker, J. Org. Chem., 27,4331 (1962).

134. C.G. Overberger, H. Ringsdor! and B. Avchen, J. Org. Chem., 30, 3088 (1965).

135. T.P. Johnston and A. Gallagher, J. Org. Chem., 22, 2442 (1964).

136. T.P. Johnston and R.D. Elliott, J. Org. Chem., 32, 2344 (1967).

137. D.L. Klayman, J.J. Maul, G.W.A. Milne, J. Heterocycl. Chem., 5, 517 (1968).

138. L. Field and J.D. Buckman, J. Org. Chem., 33, 3865 (1968).

139. A.F. Ferris and B.A. Schutz, J. Org. Chem., 28, 3140 (1963).

140. University of Illinois, Annual Progress Report, April 1, 1967-March 31, 1968,Contract No. DA-49-193-MD-2047.

141. F.I. Carroll, H.M. Dickson and M.E. Wall, J. Org. Chem., 30, 33 (1965).

142. B.J. Sweetman, M.M. Vestling, S.T. Ticaric, P.L. Kelly, and L. Ficld, J. Med. Chem.,

14, 868 (1971).

143. J.R. Piper and T.P. Johnston, J. Org. Chemn., 28, 981 (1963).

144. Parke, Davis & Company, Annual Progress Report No. 4. September 1,1965-August 31, 1966, Contract No. DA-49-193-MD-2306.

145. Esso Research and Engineernng Company, Annual Technical Report No. 3, June 1,1966-May 31, 1967, Contract No. DA-49-193-MD-2608.

146. A.F. Ferris and B.A. Schutz, J. Org. Chem, 29 201 (1964).

147. Southern Research Institute, Annual Progress Report No. 7468-1112-4V, July 1,1964-June 30, 1965, Contract No. DA-49-193-MD-2028.

148. Parke, Davis & Company, Ar.nual Progress Report No. 8, September 1, 1969-August 31, 1970, Contract No. DA-49-193-MD-2306.

149. Indiana University, FLal Report, October 1, 1960-Jan.L-v 1, 1961, Contract No.DA-49-193-MT)-2108.

661

150. Kansas State University, Final Report, July 1, 1959-July 1, 1963, Contract No.

DA.49-193-MD-2026.

151. H.F. Herbrandson and R.H. Wood, J. Med. Chem., 12,617 (1969).

152. University of California, Final Report, 1965, Contract No. DA-49-193-MD2145.

153. J.D. Buckman, B.S. Johnson and L. Field, Can. J. Microbiol., 1.,2 1263 (1966).

154. J.R. Piper and T.P. Johnston, U.S. Patent 3,892,824, July 1, 1975. Assigned toSouthern Research Institute.

155. W.O. Foye and R.H. Zaim, J. Pharm. Sci., 53,906 (1964).

156. T.P. Johnston, C.R. Stringl~llow and J.R. Piper, J. Med. Chem., 11, 1256 (1968).

157. Parke, Davis & Company, Annual Progress Report No. 6, September 1,1967-August 31, 1968, Contract No. DA-49-193-MD-2306.

158. J.R. Piper, L.McC. Rose and TI'. Johnston, J. Org. Chem., 37,4476 (1972).

159. D. Rosenthal, G. Brandrup, K.H. Davis, Jr., and M.E. Wall, J. Org. Chem., 30, 3689(1965).

160. University of Illinois, Final Report, May 31, 1965, Contract No. DA-49-193-MD-2212.

161. D.L. Klayman and W.F. Gilmore, J. Med. Chem.,7, 823 (1964).

162. Michigan Chemical Corporation, Final Report, October 26, 196 1, Contract No.DA-49-193-MD-2036.

163. S.D. Turk, R.P. Louthan, R.L. Cobb, and C.R. Bresson, J. Org. Chem., 29,974(1964).

164. F.I. Carroll, J.D. White and M.E. Wall, J. Org. Chem., 28, 1236 (1963).

165. Esso Research and Engineering Company, Annual Technical Report No. 2, June 1,1965-May 31, 1966, Contract No. DA-49-193-MD-2608.

166. W.O. Foye and J.M. Kauffman, J. Pharm. Sci., 57, 1614 (1968).

167. L. Field and R.B. Barbee, J. Org. Chem, 34, 1792 (1969).

168. J.R. Piper, L.M. Rose, T.P. Johnston, and M.M. Grenan, J. Med. Chem., 18, 803(1975).

169. J.R. Piper, C.R. Stringfellow and T.P. Johnston, J. Med. Chem., 12, 244 (1969).

170. T.P. Johnston and A. Gallagher, J. Org. Chem., 28, 4305 (1963).

171. Ohio State University, Report No. 1092-3, January 1, 1 963-June 30, 1964, ContractNo. DA-49-193.MD-2104.

662

172. University of Cincinnati, Final Report, October 7, 1974, Contract No. DADA17-69-

C-9107.

173. L. Field and J.D. Buckman, J. Org. Chem., 33,3467 (1967).

174. Rensselaer Polytechnic Institute, Final Technical Report, September 1, 1959-August 31, 1965, Contract No. DA49-193-MD-2058.

175. Y.H. Khin and L. Field, 1. Org. Chem., 37, 2714 (1972).

176. Submitted by Dr. D.C. Dittmer, Syracuse University.

177. H. Barrera and R. E. Lyle, 3. Org. Chem., 27, 641 (1962).

178. L. Goodman and J.E. Christensen, J. Org. Chan., 28, 2610 (1963).

179. Phillips Petroleum Company, Report for Period October 1, 1962-September 30,1963, Contract No. DA-49-193-MD-2069.

180. J.E. Christensen and L. Goodman, J. Org. Chem., 28, 2995 (1963).

181. D.L. Klayman, M.M. Grenan and D.P. Jacobus, J. Med. Chem., 13, 251 (1970).

182. W.M. zuReckendorf and W.A. Bonner, J. Org. Chem., 26,4596 (1961).

183. O.L. Salemni, R.N. Clark and B.E. Smart, J. Chem., Soc. (C), 645 (1966).

184. Submitted by University of New Hampshire, Contract No. DA-49-193-MD-2034.

185. University of Rochester, Final Report, Contract No. DA-49-193-MD-2031.

186. American Agricultural Chemical Company, Final Technical Report, July 1, 1961-June 30, 1962, Contract No. DA-49-193-MD-2175.

187. T.L. Fridinger and J.E. Robertson, J. Med. Chem., 12, 1114 (1969).

188. Southern Research Institute, Annual Progress Report N -. 10125-2 133-1 (1969-1970),Contract No. DADA17-69-C-9033.

189. A.P. Parulkar and L. Bauer, J. Heterocycl. Chem., 3,472 (1966).

190. University of Illinois, Annual Progress Report, July 1, 1964-June 30, 1965, ContractNo. DA.49-193-MD-2047.

191. W.O. Foye and D.H. Kay, J. Pharm. Sci., 5.1, 1098 (1962).

192. Parke, Davis & Company, Annual Progress Report No. 2, August 1. 1963-August 31,1964, Contract No. DA-49-193-MD-2306.

193. Vanderbilt University, Annual Progress Report No. 2, July 1, 1961-September 30,1963, Contract No. DA-49-193-MD-2030.

194. J.E. Christensen and L. Goodman, J. Org. Chem., 28, 847 (19( 3).

663

195. A.F. Ferrs, O.L Salami and B.A. Scutz, J. Med. Chem.,_9,391 (1966).

196. L Field, H. Hide, T.C. Owen, and A. Ferfetti, J. Org. Chem., 29, 1632 (1964).

197. L. Field and H.K. Kim, J. Org. Chin., 31,597 (1966).

198. Michigan Chemical Corporation, Annual Report, July 1959-July 1960, Contract No.DA-49-193-MD-2036.

199. Monsanto Research Corporation, Fourth Annual Progress Report, April 1, 1963-March 31, 1964, Contract No. DA-49-193-MD-2109.

200. Submitted by the University of Rochester, Contract No. DA-94-193-MD-2031.

201. L. Field, T.C. Owen, R.N. Crenshaw, and A.W. Bryan, J. Am. Chan. Soc. 83,4414(1961).

202 D.L. Klayman, J.D. White and T.R. Sweeney, J. Org. Chem., 29,3737 (1964).

203. L. Field, A. Ferretti, R.R. Crenshaw, and T.C. Owen, J. Med. Chem., 7, 39 (1964).

264. Vanderbilt University, Annual Report No. 1, July 1, 1969-June 30, 1970, ContractNo. DADA I7-69-C-9128.

205. J.R. Piper, C.R. Stringfellow and T.P. Johnston, J. Med. Chem., 9, 563 (1966).

206. Southern Research Institute, Annual Progress Report No. 10125-2133-Il (1970-1971), Contract No. DADA I7-69-C-9033.

207. Monsanto Research Corporation, Second Annual Progress Report, April 1, 1961-March 31, 1962, Contract No. DA49-193-MD-2109.

208. L. Field, A. Ferretti, and T.C. Owen, J. Org. Chem., 29, 2378 (1964).

209. Parke, Davis & Company, Annual Progress Report No. 1, October, 1963, ContractNo. DA-49-193-MD-2306.

210. S.J. Brois, J.F. Pilot and H.W. Barnum, J. Am. Chem. Soc., 92, 7629 (1970).

211. Monsanto Research Corporation, Third Annual Progress Report, April 1, 1962-March 31, 1963, Contract No. DA-49-193-MD-2109.

212. Submitted by University of Illinois, Contract No. DA-49-193-MD-2212.

213. J.A. Montgomery, R.W. Balsiger, A.L. Fikes, and T.P. Johnston, J. Org. C'bem., 27,195 (1962).

214. L. Bauer and L.A. Gardella, Jr., J. Org. Chem., 26, 82 (1961).

215. T.P. Johnston and A. Gaflagher, J. Org. Chem., 27, 2452 (1962).

216. Submitted by Monsanto Research Corporation, Contract No. DA-49-193-MD-2109.

217. Submitted by the University of Pennsylvania, Contract No. DA-49-193-MD-2035.

664

218. J.E. Christensen, and L. Goodman, J. Am. Chem. Soc., 83, 3827 (1961).

219. Submitted by Dr. H.P. Tipnts, University of Bombay, India.

220. Submitted by Stanford University, Contract No. DA-49-193-MD-2070.

221. University of Illinois, Final Report, August 16, 1959-March 31, 1969, Contract No.DA-49-193-MD-2047.

222. Kansas State University, Annual Report, July 1, 1 961 -June 30, 1962, Contract No.DA-49-193-MD-2026.

223. R.D. Elliot, J.R. Piper, C.R. Stringfellow, and T.P. Johnston, J. Med. Chem., 15595 (1972).

224. R.D. Westland, R.A. Cooley, J.L. Holmes, J.S. Hong, M.H. Lin, M.H. Zwiesler, andM.M. Grenan, J. Med. Chem., 16, 319 (1973).

225. L. Field, W.S. Hanley and I. McVeigh, J. Med. Chem., 14,995 (1971).

226. R.D. Westland, J.L. Holmes, M.L. Mouk, D.D. Marsh, R.A. Cooley, and J.R. Dice,J. Med. Chem., 11, 1190 (1968).

227. L. Goodman and J.E. Christensen, J. Am. Chem. Soc., 83, 3823 (1961).

228. L. Goodman and J.E. Christensen, J. Org. Chem., 28, 158 (1962).

229. W.M. zuReckendorf and W.A. Bonner, Tetrahedron, 1, 1721 (1963).

230. J.R. Piper, L.M. Rose, A.G. Laseter, T.P. Johnston, and M.M. Grenan, J. Med. Chem.,17,1119 (1974).

231. Monsanto Research Corporation, First Annual Progress Report, April 1, 1960-March 31, 1961, Contract DA-49-193-MD-2109.

232. Submitted by Kansas State University, Contract No. DA-49-193-MD-2026.

233. B. Buchner and G.G. Curtis, U.S. Patent 3,286001, November 15, 1966. Assignedto Continental Oil Company.

234. S.F. Thames and L.H. Edwards, J. Heterocycl. Chem., 5, 115 (1968).

235. Phillip Petroleum Company, Final Report, October 1, 1959-January 31, 1965,Conti ;t No. DA-49-193-MD-2069.

236. Indiana University, Final Technical Report, February 1, 1960-August 30, 1963,Contract No. DA-49-193-MD-2096.

237. E. Campaigne and P.K. Norgund, J. Org. Chem., 29, 224 (1964).

238. D.L. Klayman, R.J. Shine and A.S. Murray, J. Pharm. Sci., 59 1515 (1970).

239. D.L. Klayman and W.F. Gilmore, U.S. Patent 3,655,715, April 11, 1972. Assignedto U.S.A.

665

240. SI. Brob and H.W. Barnum, U.S. Patent 3,574,698, April 13, 1971. AssIgned to EssoResearch and Engineering Company.

241. S.J. Brols, U.S. Patent 3,476,833, November 4, 1969. Assigned to Esso Resemrch andEngineering Company.

242. S.J. Brois, U.S. Patent 3,468,925, September 23, 1969. Assigned to Esso Researchand Engineering Company.

243. S.J. Brois, U.S. Patent 3,501,557, March 17, 1970. Assigned to Esso Research andEngineering Company.

244. Submitted by University of Southern Mississippi, Contract No. DA-49-193-MD-29 10.

245. L. Field and P.R. Engelhardt, J. Org. Chem., 35, 3647 (1970).

246. L. Field and P.M. Giles, Jr., J. Med. Chem., 13, 317 (1970).

247. L. Field and H.K. Kim, J. Med. Chem., 9, 397 (1966).

248. L. Field, T.F. Parsons and D.E. Pearson, J. Org. Chem., 31,3550 (1966).

249. B.-T. Ho and W.C. McCarthy, J. Pharm. Sci., 5_6, 648 (1967).

250. W.C. McCarthy and B.-T. Ho, J. Org. Chem., 26,4110 (1961).

251. C.W. Schimelpfenig, J. Org. Chem., 27, 3323 (1962).

252. S.-H. Chu and H.G. Mautner, J. Org. Chem., 26,4498 (1961).

253. University of Cincinnati, Final Report, October 7, 1974, Contract No. DADA17.-69-C-9 107.

254. Polytechnic Institute of Brooklyn, Annual Progress Report, March 1, 1962-February 28, 1963, Contract No. DA-49-193-MD-2032.

255. P.K. Srivastava and L. Field, J. Med. Chem., 16,428 (1973).

256. J.R. Piper, C.R. Stringfellow and T.P. Johnston, J. Med. Chem., 14,350 (1971).

257, T.C. Owen, C.L. Gladys and L. Field, J. Chern. Soc., 501 (1962).

258. L. Field and Y.H. Khirn, J. Med. Chem., 15,312 (1972).

259. T.P. Johnston, C.R. Stringfellow and A. Gallagher, J. Org. Chem., 27, 4068 (1962).

260. N.E. Heimer and L. Field, J. Org. Chem., 35, 3012 (1970).

261. General Aniline and Film Corporation, Final Report, July 1, 1961 -September 30,1962, Contract No. DA-49-193-MD-2173.

262. W.A. Bonner and W.M. zuReckendorf, Chem. Ber., 94, 225 (1961).

665

263. Washington State University, Final Technical Report, August 1, 1959-August 31,1965, Contract No. DA49-193-MD-2049.

264. Southern Research Institute, Annual Progress Report, No. 7920-1112-V, July 1,

1965-June 30, 1966, Contract No. DA-49-193-MD-2028.

265. Submitted by University of Illinois, Contract No. DA-49-193-MD-2047.

266. University of Arizona, Final Technical Report, September 1, 1959-August 31, 1961,Contract No. DA-49-193-MD-2033.

267. Stanford Research Institute, Annual Summary Report and Final Report, October 1,1962-March 31, 1964, Contract No. DA-49-193-MD-2068.

268. R.D. Elliot and T.P. Johnston, J. Med. Chem., 12, 253 (1969).

269. Southern Research Institute, Final Report, DORI-KM-73-201, 1969-1973, ContractNo. DADA-69-C-9033.

270. J.R. Piper, C.R. Stringfellow and T.P. Johnston, J. Med. Chem., 14, 1212 (1971).

271. S.F. Thames and L.H. Edwards, J. Chem. Soc. (C), 2339 (1968).

272. Submitted by Purdue University, Contract No. DA-49-193-MD-2107.

273. University of Maryland, Final Technical Report, July 1, 1964-March 31, 1966,Contract No. DA-49-193-MD-2609.

274. D.L. Klayman, R.J. Shine and J.D. Bower, J. Org. Chem., 37, 1532 (1972).

275. University of Illinois, Annual Progress Report, July 1, 1966-March 31, 1967,Contract No. DA-49-193-MD-2047.

276. R.R. Crenshaw and L. Field, J. Org. Chem., 30, 175 (1965).

277. Submitted by Dr E.L. Eliel, University of Notre Dame.

278. Submitted by Southern Research Institute, Contract No. DA-49-193-MD-2028.

279. L. Field, C.B. Hoelzel and J.M. Locke, J. Am. Chem. Soc., 84,847 (1962).

280. 3.M. Barton and L. Bauer, Can. J. Chem., 47, 1233 (1969).

281. W.M. zuReckendorf and W.A. Bonner, Chem. Ber., 94,2431 (1961).

282. University of Illinois, Annual Progress Report, July 1, 1965-March 31, 1966,Contract No. DA-49-193-MD.2047.

283. R. Mani, W.M. zuReckendorf and W.A. Bonner, Chem. Ber., 95, 1000 (1962).

284. James S. Todd, Ph.D. Thesis, University of Rochester, 1960.

285. R.D. Westland, U.S. Patent 3,453,309, July 1, 1969. Assigned to Parke, Davis &Company.

667

286. R.D. Wetlmnd, U.S. Patent 3,413,330, November 26, 1968. Assigned to P•rke, Davi& Company.

287. D.L. Klayman and W.F. Gilmore, U.S. Patent 3,595,899, July 27, 1971. Assigned toU.S.A.

288. J.R. Piper and T.P. Johnston, J. Org. Chem., 33,636 (1968).

289. Submitted by the University of Maryland, Contract No. DA-49-193-MD-2609.

290. Submitted by Dr. Lamar Field, Vanderbilt University.

291. G.M. Singerman, J.L. Kimura and R.N. Castle, J. Heterocycl. Chem.,_3, 74 (1966).

292. S.F. Thames and J.E. McClesky, J. Heterocycl. Chem., 4,371 (1967).

293. R.D. Westland, U.S. Patent 3,408,381, October 29, 1968. Assigned to Parke, Davis& Company.

294. R.D. Westland, U.S. Patent 3,453,308, July 1, 1969. Assigned to Parke, Davis &Company.

295. Parke, Davis & Company, Annual Progress Report No. 3, February 1966, ContractNo. DA-49-193-MD-2306.

296. Submitted by Stanford Research Institute, Contract No. DA-49-193-MD-2068.

297. A.F. Ferris, O.L. Salerni and B.A. Schutz, J. Chem. Soc., 6650 (1965).

298. R.D. Westland, M.H. Lin, R.A. Cooley and M.L. Zwiesler, J. Med. Chem., 16,328(1973).

299. R.D. Westland, M.M. Merz, S.M. Alexander, L.S. Newton, L. Bauer, T.T. Conway,J.M. Barton, K.K. Khullar, P.B. Devdhar, and M.M. Grenan, J. Med. Chem., 15, 1313(1972).

300. University of Illinois, Annual and Progress Report, April 1, 1969-August 31, 1970,Contract No. DADA 17-69-C-91 10.

301. The Epoxylite Corporation, Final Progress Report, April 1, 1966-March 31, 1967,Contract No. DA-49-193-MD-29 14.

302. S.L. Holton, J.E. Christensen, O.P. Crews, and L. Goodman, Can. J. Chem., 42, 2147(1964).

303. Submitted by Ohio State University, Contract No. DA-49-193-MD-2104.

304. K.V. Bhat and W.C. McCarthy, J. Pharm. Sci., 53, 1545 (1964).

305, Submitted by Dr. E.E. Sisman, University of Kansas.

306. J.R. Piper, C.R. Stringfellow, R.D. Elliott, and T.P. Johnston, J. Med. Chem., 14,345 (1971).

668

307. Midwest Research Institute, Annual Progress Report No. 4, November 1, 1964-December 31, 1965, Contract No. DA-49-193-MD-2174.

308. Vanderbilt University, Annual Report No. 7, October 1, 1967-September 30, 1968,Contract No. DA-49-193-MD-2030.

309. T.F. Parsons, J.D. Buckman, D.E. Pearson, and L. Field, J. Org. Chem., 30, 1923(1965).

310. University of New Mexico, Final Report, August 1, 1964-December 31, 1965,Contract No. DA-49-193-MD-2645.

311. K.K. Khullar and L. Bauer, J. Org. Chem., 36, 3038 (1971).

312. Rensselaer Polytechnic Institute, Annual Progress Report, September 1, 1963-August 31, 1964, Contract No. DA-49-193-MD-2058.

313. Monsanto Research Corporation, Seventh Annual Report, April 1, 1966-March 31,1967, Contract No. DA-49-193-MD-2109.

314. W.O. Foye, E.F. Lasala, M. Georgiadis, and W.L. Meyer, J. Pharm. Sci., 54, No. 4,557 (1965).

315. R.D. Westland, E.R. Karger, B. Green, and J.R. Dice, J. Med. Chem., 11,84 (1968).

316. L. Field and T.F. Parsons, J. Org. Chem., 3.0, 657 (1965).

317. J.D. Buckman, M. Bellas, H.K. Kim, and L. Field, J. Org. Chem., 32, 1626 (1967).

318. Submitted by Dr. H.P. Tipnis, University of Bombay, India.

319. G.W. Stacy, A.J. Papa, F.W. Villaescusa, and S.C. Ray, J. Org. Chem., 29, 607 (1964).

320. G.W. Stacy, A.J. Papa and S.C. Ray, J. Org. Chem., 26,4779 (1961).

321. Yale UnP'!emity, Terminal Report, Contract No. DA-49-193-MD-2106.

322. PX. Snvasta-a and L. Field, J. Org. Chem., 37,4196 (1972).

323. P.K. Srivastava, L. Field and M.M. Grenan, J. Med. Chem., 18, 798 (1975).

324. R.D. Westland, M.L. Mouk, J.L. Holmes, R.A. Cooley, Jr., and J.S. Hong, J. Med.Chem., 15,968 (1972).

325. R.D. Elliot and T.P. Johnston, J. Med. Chem., 12, 507 (1969).

326. University of New Hampshire, Final Report, September, 1962-September, 1963,Contract No. DA-49-193-MD-2034.

327. A.F. Ferris and B.A. Schutz, J. Org. Chem., 28, 71 (1963).

328. L. Field and W.B. Lacefield, J. Org. Chem., 31, 599 (1966).

669

329. Submitted by Drug Development Branch, Drug Reusarch and Development Program,

Division of Cancer Treatment, National Cancer Institute.

330. Submitted by the Prevention of Deterioration Center, National Research Council.

331. D. Horton and M.L Wolfrom, J. Org. Chem., 27, 1794 (1962).

332. M.L. Wolfrom, W.A. Cramp and D. Horton, J. Org. Chem., 29,2302 (1964).

333. L. Field and P.M. Giles, Jr., J. Org. Chem., 36, 309 (1971).

334. W.M. zuReckendorf and W.A. Bonner, J. Org. Chen., 26, 5241 (1961).

335. M.L. Wolfrom, W.A. Cramp and D. Horton, J. Org. Chem., 30(19), 3056 (1965).

336. O.L. Salerni and R.N. Clark, J. Med. Chem.,9_, 778 (1966).

337. Submitted by University of Kentucky, Contract No. DA-49-193-MD-2054.

338. Submitted by Dr. Leonard M. Rice, Howard University.

339. L. Field, H.K. Kim and M. Bellas, J. Med. Chem., 1_0 1166 (1967).

340. Submitted by Thiokol Chemical Corporation, Contract No. DA-49-193-MD-2053.

341. K.R. Henery-Logan and S. Abdou-Sabet, J. Org. Chem, 38, 916 (1973).

342. T.P. Johnston and A. Gallagher, J. Org. Chem., 28, 1305 (1963).

343. D.L. Klayman and T.S. Woods, Intemat. J. of Sulfur Chemistry, 8, 5 (1973).

344. W.A. Bonner and P.I. McNamee, J. Ors. Chem., 26,2554 (1961).

345. D. Horton and M.L. Wolfrom, J. Org. Chem., 27, 1794 (1962).

346. M.L. Wolfrom, D. Horton and D.H. Hutson, J. Org. Chem., 28, 845 (1963).

347. M. Bellas, D.:L. Tuleen and L. Field, J. Org. Chem., 32, 2591 (1967).

348. P.K. Srivastava. L. Field and M.M. Grenan, J. Med. Chem., 18, 798 (1975).

349. D.L. Klayman, Biochemical Preparations, J.H. Law, Editor, Vol. 13. 84, John Wileyand Sons, New York, NY, 1971.

350. L. Field, W.S. Handley, I. McVeigh, and Z. Evans, J. Med. Chem., 14,202 (1971).

670

STRUCTURE-ACTIVITY RELATIONSHIPS

The decision having been made to study the modification of MEA and MFA in an

attempt to incrc:-•, effectiv.ness and decrease toxicity, compounds were synthesized which

involved modii.t; n of the amino moiety, the backbone between the N and S atoms and

the thiol moieLy.

In this S-A discussion an attempt will be made to draw broad conclusions where there

seems to be sufficient support from the data. While this will often be difficult and incomplete

because of the scattering of structural variations and the nature of the testing, the effort

would seem to be justified because such generalization would be useful in a field where think-

ing is usually centered upon individual compounds. The activities referred to will be those

from intraperitoneal administration of the compound unless oral administrailon is specifically

indicated.

The Thiol Blocking Concept

Early in the drug development program the data indicated that an active compcound

would possess a sulfhydryl or a physiologically potential sulfhydryl group separated by twoor three carbon atoms from a basic nitrogen function. Blocking of the thiol group in a way

such that it became unavailable metabolically, e.g., as a thioether, resulted in inactive com-pounds. It also became apparent that the relative activity and toxicity within a series of

otherwise identical compounds can be markedly affected by the nature of the sulfhydryl-

latentiating group; thus the order of toxicity and activity c f one series of compounds may be

the complete reverse of another with the identical sulfur-blocking groups. Three such series

are shown, by way of illustration, in Tables 1, 2 and 3; other series could be similarly de-veloped. Doses and approximate LD5 0s (ALD50 ) are presented on a molar basis to facilitate

comparison. In the series of amide derivatives shown in Table 1 the thiol was the least toxic

and the phosphorothioate the most toxic whereas in the series of diamines shown in Table 2,

the phosphorothioate was the least toxic and the disulfide* the most toxic with the thiol

the next most toxic. In comparing the activities of members of the series of Table I it is seen

that the thiol was most active, effecting good protection at about one fourth of its ALD50

whereas the phosphorothioate gave no protection at nearly one half of its ALD50 . With the

diamines, on the other hand, Table 2, the phosphorothioate was the most active, giving

*It should be kept in mind that the unblocking of a thiol in the form of a disulfide, unlikethe unblocking of other thiol functions, yields two molecules of thiol for each disulfide mole-cule if the unblocking is a reductive process.

671

complete protection at ceow than one third of the ALD5 0 and appreciable protection at about

one seventh of the ALDs 0 ; the thiol on the other hand was inactive at one third of its

ALD50 and the thiosulfuric acid (Bunte salt) was inactive at two thirds of its ALDs 0 . In con-

trast to the highiy polar, water soluble series of diamines, Table 2, where the Bunte salt was

relatively non toxic compared to the disulfide, the introduction of the highly lipid solubiliz-

ing decyl group produced a series, Table 3, in which the Bunte salt, WR-1607, was the most

toxic member of the series, being on the order of 6 times as toxic as the thiol; in contrast, in

the amide series, Table 1, the Bunte salt was only about 1.3 times as toxic as the thiol and in

the diamine series, Table 2, it was only about one half as toxic. The decyl compound,WR-1607, was however, in contrast to the very polar diamine, WR-9720, Table 2, very active

both relative to the ALD50 and in the absolute (mg) dose. It was thus neceseary to synthesizeand test a number of the sulfur-blocked analogs for each promising moiety that was attached

to the amino group of MEA. Altogether about 50 different sulfur-blocking moieties were ex-

amined in the course of the program but the highest activity was usually found among the

thiols, disulfides, thiosulfuric acids or phosphorothioic acids. These classes, therefore, re-ceived the most attention in the synthetic effort and necessarily form the basis of thestructure-activity analysis.

The data presented above indicate that the mode of action of these compounds is com-

plex. Because of the greater in vivo lability of the various thiol-blocked moieties comparedto the N-substituted end of the MEA molecule, the blocked thiols have been considered asprodrugs, the blocking group controlling such factors as the rate of In vivo release of theactive thiol, the toxicity, and membrane passage; thus the blocked thiols were associated withthe drug delivery system whereas the N-substituents were associated with modification of theinherent antiradiation properties of MEA. While such a compartmentalization of effects is agross over-simplification, the concept was useful in the practical program. Substituents on thethiol-blocking group far removed from the actual thiol-blocking bond can also have a marked

effect. For example WR-77,548, CH3CONHCH 2CH2SS(CH 2 )3 CH2SO 2 H, gave essentiallycomplete protection at about 1/15th of its ALD5 0 whereas WR-76,844, the correspozidingsulfonic acid, CH3CONHCH2 CH2 SS(CH2 )3CH2SO3H, gave only fair protection at two

thirds of its ALDS0 and was inactive at one third of this .lose.

3-Aminopropanethiols and Derivatives

In general, the data indicate that, in the aminoalkylthiol-type compounds, a two

carbon chain between N and S confers optimal antiradiation activity. Increasing the chain

672

length beyond three carbons abolishes activity. With relatively few, but perhaps important,exceptions, discussed below, activity of the 3-e-ninopropanethiol types was low or non-existent. This generalization has been amply verified by testing numnrous compounds in

which 3-aminopropanethiol has been substituted both on the nitrogen and on the backbone,

including compounds in which vicinal carbons in the backbone have been incorporated in a

cycloalkane moiety; one exception, cts-2-fnercapto-cycloLutylmethylamine, WR-192-526, did

have appreciable, 'iut not outstanding activity. The 3-aminopropanethiosulfuric acids, in-

cluding those with a variety of substitutions, were also inactive. However, when a hydroxy

group is inserted in the backbone, I.e., 2-hydroxy-3-aminopropanethiosulfuric acid, a number

of the simple N-n-alkyl derivatives of the hydroxylated form, but not the parent hydroxyl-

ated compound, showed activity. There seemed to be no pattern to the activity and the best

compound was the N-octyl homolog, WR-l 42,911. The 3-aminopropylphosphorothioates

followed the same pattern as the Bunte salts. However, the parent compound, WR-35,978,

while inactive at tolerated doses, car. be converted to very active derivatives by the introduc-

tion of a 2-hydroxy or 2-amino group on the backbone, WR-77,913 and WR-l 14,391 respec-

tively. The former compound, WR-77,913, was particularly noteworthy. In addition to thesemodifications, the substitution of certain aminoalkyl groups on the amino group of theparent, i.e., RNH(CH 2 )nNHCH 2 CH2 CH 2SPO 3H2 , resulted in very active compounds (Table39). Finally, there can be activity when the basic nitrogen function is three carbons removed

from the sulfur if the basic function is an amidino group (Table 46).

Backbone Substitutions (Tables 4-10)

If the amino function does not terminate a chain in the aminoethanethiols, i.e.,

H2 N&CH 2SH (Table 4), where R is alkyl and R2 is H, appreciable, but varied, activity wasR2

retained when R is not larger than propyl; where R is alkyl and R2 is methyl, activity waslowered or abolished and when RI and R2 form part of a carbocycle, activity was alsoabolished. The same generalization %.an be made for the corresponding thiosulfates (Table 5);however, in this class the compounds were inactive when R1 is larger than ethyl. The two car-bocyclic thiosulfates, WR-2649 and WR-2579, did show some activity as opposed to the cor-

responding thiols but this activity was at the expense of higher test doses which were useAbecause of the lower toxicity. In general, the toxicity of the thiosulfates was lower than the

thiols and comparable to the phosphorothioates (Table 6). The data on the latter class are

673

very limited but, aside from the greater activity of the parent compound compared to the

parents cf the other two classes, the trend in activity would seem to be the same.

RI

When the thiol function does not terminate a chaLn, i.e., H2NCH 2(4SH (Table 7),

activity was abolished when RI is larger than methyl and R2 was hydrogen. Stereoisomerism

seems to be unimportant. When the thiosulfate group does not terminate a chain, i.e.,RI|

H2 NCH2 HSSO3 H (Table 8), the compounds were, again, less toxic than the corresponding

thiols but activity ended early in the series.

When neither the amino nor the sulfur function terminates the chain, i.e.,

RIR 2

H2N(PH&HSH, activity was absent. However, when RI and R2 form part of a carbocycle,

e.g., 2-aminocyclobutanethiol, 2-aminocyclopentanethiol, etc., activity was restored. The ac-

tivity fell off as ring size increased from cyclobutane through cyclohexane; cis 2-aminocyclo-

butanethiol had about the same activity as aminoethanethiol. The cis isomer seemed some-

what better than the trans in each case. There are not enough thiosulfates of this type to

draw conclusions.Functionalization of the alkyl group R1 and R2 in the H2NC(RIR 2 )CH2SH series

either by hydroxylation or thiolation lead to profound changes in toxicity and reactivity(Table 9). Thus when Rl is -CH2 SH, the 1,3-propanedithiols, the compounds were generally

qu, ite toxic regardless of the nature of R2 and more toxic than the corresponding unfunc-

tionalized compounds in the few cases where comparisons can be made. When both R1 and

R2 are hydroxymethyl, the compound was much superior to the corresponding one where

the methyl groups are unsubstituted. The compound with an aminoalkyl group, WR-193,702,

was highly active but this type of structure was explored only in the corresponding phos-

pborothioate series (Table 10). The compounds in the latter group were all highly active and

of relatively low toxicity. While there is a paucity of the corresponding functionalized deriva-

tives in the thiosulfuric acid series, a comparison of WR-2389, WR-2917 and WR-1 76,241,

Tables 9 and 10, illustrates what is generally true: the water soluble polyhydroxyalkyl or

polyaminoalkyl types are least active when the sulfur-containing function is in the form of a

thiosulfuric acid. There are insufficient data of the type H2NCH 2C(RI R,)SH where RI and

R2 are functionalized to justify comment.

674

N.Alkylaminoethanethiols and Derivatives (Tables I I and 12)

The n-alkylan-inoethanethiosulfuric acids, RNHCH2CH2 SSO3 H, showed an interesting

triphasic pattern of activity as R is increased in the homologous series to 18 carbons (Table

I I). The first three members of the series, R = methyl, ethyl and propyl were active. The

next four, R = C4 thru C7 were inactive but activity was again evident in the series when

R = C8 thru CI 0 . With further extension of the series the activity disappeared except for

some low activity shown by the R = C13 and R = C14 homologues. This homologous series

of n-alkylaminoethanethiosulfuric acids progresses from the more water soluble members to

the water insoluble; the toxicity increased as the molecular weight increased and reached a

maximum in the range of R = C 0I.-C 14 , after which it diminished. The most active members

of the series, other than the first few members, were characterized by a relatively high effi-

ciency in terms of milligrams required for protection when the compounds are administered

parenterally. They were inactive when administered orally which suggests that they are not

well absorbed. The efficient intraperitoneal activity is compromised somewhat by the rela-

tively high toxicity. A number of the alkylaminoethanethiosulfuric acids have been found to

produce a generalized vasoconstriction and myocardial depression in the dog which resulted

in hypertension, slowed heart rate and narrowed pulse pressure. In addition, the n-decyl

homolog (R = C10 ), WR-1607, was found to possess k-adrenergic blocking action.

In a fair number of examples, with only two exceptions, isomerization of the normal

alkyl chain of the alkylaminoethanethiosulfuric acids resulted in retention or enhancement of

activity in those cases where the corresponding normal chain was active, I.e., in the octyl-,

nonyl-, and decyl- aminothiosulfuric acids (Table 12). In the only example of the isoneriza-

tion of the undecyl chain, WR-241 1, activity was found in contrast to the normal isomer. No

activity was seen in compounds where the nitrogen was tertiary, either in the dialkylamino

type or when the nitrogen atom was incorporated in a ring. N-acylated compounds were also

inactive. The introduction of an alkyl or phenyl group on the backbone of the aminoethane-

thiosulfuric moiety had no effect on the activity of those compounds that were inactive with-

out such substituents; of the few active compounds that were so modified, WR-1607,

WR-258 and WR-3548, activity was abolished.

The corresponding homologous series of n-alkylaminoethanethiols, RNHCH 2CH 2 SH,

(Table 11), closely, but not exactly, paralleled the pattern of activity of the Bunte salts. Thus

the activity in the short chain homologues does not extend as far in the thiol series as in

the Bunte salt series, i.e., R = C, versus C3 . In addition, the second peak of activity extends

from R = C8 thru R = CI I; further elongation of the chain produced no third peak of low ac-

tivity as in the Bunte salt series.

675

As is the case with the alkyazminoethanethiosulfuric acids isomerization of a normal

alkyl chain with 7 or fewer carbons in the alkylaminoethanethiol series had no salutary effect

(Table 12). Unfortunately there is a paucity of thiols with isomerized alkyl groups containing

8, 9, 10 or I I carbons for comparison with the thiosulfunc acids. However, the few data that

are available suggest that they are not as toxic nor are they as active as the thiols with normal

chains. The introduction of an alkyl, hydroxyalkyl, or phenyl on the two-carbon backbone of

the aminoethanethiol moiety in the n-alkylaminoethanethiols abolished activity. Tertiary

aminjethanethiols, either the dialkylamino type or those in which the N atom is a part of a

ring were uniformly inactive.

The alkylaminoethylphosphorothioates, as a series, were not studied to the extent of

the thiosulfuric acids or thiols. From limited data it would appear that, in their pattern of ac-

tivity, they were more like the thiosulfuric acids than the thiols. In the few direct compari-

sons possible in the range of alkyl groups that confer activity, they were, at least, as active or

more active than the corresponding thiosulfuric acids. Compound WR-75232, for example,

was particularly active.

Relatively few of the alkylaminoethanedisulfides were obtained. The potent disulfide,

cystamine, WR-352, was comparable in activity to the corresponding thiol, MEA. As a class

there are insufficient data to draw any generalizations.

Phenalkylaminoethanethiols and Derivatives (Tables 13 and 14)

The homologous series of phenalkylaminoethanethiols, (Table 13), C6H5 (CH2 )n

NHCH 2CH2 SH, n = 0-4, were consistently more toxic than the corresponding thiosulfuric

acids, and, with the exception of WR-3233, had little or no intraperitoneal activity at the

doses tested; they were not tested orally. The homologous series, with or without substitu-

ents on the phenyl ring, was not carried beyond n = 4 because the corresponding thiosulfuric

acid series seemed to hold more promise, e.g., WR-2397 and WR-36956 (Table 13) vs

WR-2754 and WR-3050 (Table 14) respectively. In the homologous series of unsubstituted

phenalkylaminoethanethiosulfuric acids, Table 14, C6 H5(CH 2 )nNHCH 2CH- SSO 3 H, n = 0-6,

the first three members of the series were inactive but the other four compounds were active.

The optimum chain length was n = 4 and n = 5, both compounds showing good activity. The

introduction of methyl or ethyl groups on the phenyl ring of the phenbutyl homolog brought

about a dramatic increase in toxicity (10 to 20 times as toxic) with retention of activity at

the correspondingly low doses at which the compounds were tested. The introduction of a

4-OCH 3 substituent in the phenyl ring of the phenalkylazninoethanethiosulfuric acids had, in

general, a salutary effect on activity, especially notable in the phenbutyl analog. Branching of

676

the two-carbon spacer between the unsubstituted phenyl ring and the nitrogen of the thio-

sulfuric acids introduced no activity. No noteworthy activity was found for the relatively few

of these Bunte salts that were tested orally. The one that showed the best activity when ad-

ministered intraperitoneally, WR-3050, was inactive when administered orally.

Hydroxyalkylaminoethanethiols and Derivatives (Tables 15-20)

Monohydroxylation of the alkyl chain of the alkylaminoethanethiols, regardless of the

position of the hydroxyl group or of branching of the chain, reduced the toxicity of the com-

pound compared with the unsubstituted alkyl derivative (Table 15). The hydroxyethyl and

hydroxypropyl derivatives were active in contrast to the unsubstituted derivatives but were

tested at higher doses because of the lower toxicity. Analogs with R groups containing more

than 3 carbon atoms and bearing a single hydroxyl, with the strange exception of the 5-

hydroxypentyl analog, WR-2469, were inactive. When the nitrogen atom was made tertiary,

either by simple alkylation or doubling the hydroxyalkyl moiety, all activity was abolished.

In general when more than one hydroxyl is introduced into the alkyl chain (Table 15)

toxicity is further reduced and testing can be done at higher doses. The polyhydroxyalkyl

derivatives all gave appreciable activity, WR-2347 being outstanding. The number of possible

position isomers is so large compared to the number of compounds tested that it is essentially

impossible to generalize. It would appear, nevertheless, in comparing the hydroxy and poly-

hydroxy derivatives that isomerism does play an appreciable role.

A comparison of the activity of the hydroxyalkyl-substituted derivatives as a function

of the sulfur-blocking group can be made only tentatively because there were many more

thiols synthesized than disulfides, thiosulfuric acids or phosphorothioic acids and a direct

comparison of a series of compounds bearing the same N-alkyl moiety, but having all four

sulfur-blocking groups was usually not possible (Tables 16, 17 and 18). However, it does seem

clear that, as a class, the hydroxyalkylthiosulfuric acids are the least toxic and the disulfides

the most toxic with the thiols and phosphorothioic acids occupying an intermediate position.

With respect to activity the phosphorothioates, as a class, would appear to be the most active

while the disulfides and thiosulfuric acids are the least active. Interesting too was the

di(hydroxyethyl) derivative (WR.4122, ALD 50 = 1750) because of the activity and much

lo er toxicity compared to the unsubstituted dialkyl analog.

No noteworthy activity was seen in the hydroxyalkyl class of compounds when they

were administered orally regardless of the type of thiol blocking. The most active thiol when

administered intraperitoneally, WR-2347, was inactive when administered orally.

677

Simple alkylation of the hydroxyl group of hydroxyethyl-, or 3-hydroxypropylamino-

ethanethiols, WR-698 or WR-I 119, increases toxicity and abolishes activity (Table 19).

However, if the alkylating group contains a hydroxyl group, activity is retained with no in-

crease in toxicity. There are too few of the alkoxyalkylaminoethanethiosulfuric acids to draw

conclusions with respect to hydroxylation of the O-alkyl group but O-alkylation of the long

chain w-hydroxyalkyl derivatives does apparently increase toxicity compared to the analog

with the free hydroxyl group. The cycloalkyloxyaminoethanethiob (Table 20), with the ex-

ception of the first two compounds, WR-3069 and WR-411 , exhibited fair to good activity

over the entire range of structural variations when administe-,ed intraperitoneally. About one-

half of the active compounds were tested by oral administration and were found to be in-

active, without exception.

Phenoxyalkylaminoethanethiols and Derivatives (Tables 21-24)

In the phenoxyalkyl series many more aminoethanethiosulfuric acids (Table 22) were

synthesized than were thiols (Table 21) or disulfides (Table 23). Because of this situation,

comparisons of the three sulfur-blocking groups has to be tentative. However, when compari-

sons are possible, the thiosulfuric acids, in general, were the least toxic. When the aryloxy

moiety is attached to the nitrogen by a short chain, i.e., 2 or 3 carbons, the compounds were

invariably inactive or of very low activity, regardless of the nature of the substituents on the

ring. The most active compounds of the thiosulfuric acid series when administered intraperi-

toneally were found when the insulating methylene chain was 4, 5 or 6 carbons in length

(n = 4,5,6); the type of substituent on the ring also markedly effected activity. High activity

did not carry over to oral administration. There are an insufficient number of compounds in

the thiol or disulfide series to extend such a generalization. The thiols were of such modest

activity that the activity by oral administration was not investigated. Very few phosphoro-

thioates in this series were synthesized. The unsubstituted phenoxy analogs insulated by 2, or

3 carbons were, like their thiol and thiosulfuric acid counterparts, inactive. Where direct

comparison was possible in the aryloxybutyl series, e.g., the 2,6-(CH 3 )2C6 H3-O(CH2 )4-,

2-(CH3 )2CHC6 H4 -O(CH2 )4 - and the 3-(CH3 )2N-4-CH 3 C6 H3 -O(CH2 )4 - analogs, (WR Nos.

117 914, 117 917 and 138 736 respectively), the phosphorothioates were more toxic than

the thiosulfuric acids and were inactive. Branching of the insulating chain resulted in inactive

compounds as did doubling the aryloxyalkyl roiety on nitrogen so as to make the amine

tertiary. Although a few of the compounds in the aryloxybutyl series showed some oral ac-

tivity, the class, in general, was inactive.

678

When the aminoethanethlol moiety in a number of the phenoxyalkylrnlnoethanethiols

was tied up as an N-substituted thiazolidine in an attempt to increase oral activity, any intra-

peritoneal activity that was present in the corresponding thiosulfuric was abolished or greatly

diminished and no oral activity was evident (Table 24). A direct comparison of the phenoxy-

alkylthiazolidines with the pyridyloxyalkylthiazolidines cannot be made because of the

presence of different substituents on the pyridyl and phenyl rings.

Cycloalkylalkylain.noethanethiols and Derivatives (Tables 25-28)

Only a few compounds were synthesized with carbocyclic rings larger than seven mem-

bers in the cycloalkylalkylaminoethanethiosulfuric acid series. For normal alkyl spacers of

3, 4, 5, or 6 carbons, toxicity increases as the ring size is increased from 4 to 7 carbons

(Table 25). For any given ring size from 4 to 7 carbons, there is a point where the compounds

become appreciably more toxic as the length of the normal spacer increases. This point is

reached sooner as the size of the ring increases. The most active compounds with unbranched

alkyl spacers were clustered in the area of spacers of 4, 5, and 6 carbons and rings of 4, 5 or

6 carbons. Branching of the spacer chain between the cycloalkyl moiety and the nitrogen

atom can bring about a marked change in effectiveness and toxicity; compare, for example,

WR-2571 with WR-3562; WR-2942 with WR-6136 and WR-7466; and WR-2691 and

WR-6403 with WR-6400 (Table 24). Thus the antiradiation activity would seem to depend to

some extent upon the total number of carbon atoms in the spacer rather than entirely upon

the distance between the ring ,nd nitrogen. Although there are little data, there is the sugges-tion that the isomerism of the spacing group when both distance and total number of carbons

is held constant may play a role; compare, e.g., WR-6136, 7466 and WR-7467.

Most of the cycloalkylalkylaminoethanethiosulfuric acids that were tested by oral ad-ministration were inactive and those that were active were only fair at best even when admin-

istered at a relatively high dose (Table 25). Oral data did not correlate well with that obtained

from intraperitoneal administration.

There were not as many cycloalkylalkylaminoethanethiols synthesized as there were

the corresponding thiosulfuric acids. In general, the former were more toxic and less active

than the latter. There were not enough of the disulfides or phosphorothioates synthesized to

allow generalizations to be made. Intraperitoneal data for these classes are tabulated in

Tables 26, 27 and 28.

679

Heteroalkylamninoethanethiols and Derivatives

Regardless of the type of sulfur blocking, i.e., aminoethane-thiols, -thiosulfuric acids,

*phosphorothioates or -disulfides, compounds representing a variety of heterocycles attached

directly or through short alkyl chains to the nitrogen atom of the aminoethyl moiety, with

attachment involving either a carbon or the hetero atom of the heterocycle, showed little or

no activity in general. There were a few exceptions which showed moderate activity but no

explanation or correlation was apparent; note, for example, 3-piperidinylmethylaminoethane

phosphorothioate, WR 176,256, morpholinoethyldisulfide, WR 177,475 and 2-quinoxalinyl-

amninoethanethiosulfuric acid, WR 176,606.

Pyridyl- and quinolyloxyalkylaminoethanethiols and Derivatives (Tables 29-31)

Derivatives of the 2-aminoethanethiol-type compounds in which a 2-pyridyloxyalkyl

or 2-quinolyloxyalkyl group was attached to the nitrogen proved to be an interesting and

active series of compounds.

In a series of 2-pyridyloxyalkylaminoethanethiosulfuric acids (Table 29), the length of

the alkyl spacer as well as the nature and position of the ring substituent had a marked effect

on activity. A chain of 5 carbon atoms with a bromo or chloro g-oup in the 5 or 3,5 positions

of the pyridine moiety resulted in the best intraperitoneal activity. The effect of the position

of the ring substituent can be appreciated, for example, from a comparison of WR 43,900with WR 50,480 and WR 85,565 with WR 94,533. With one exception, WR 138,412, all of

the Bunte salts that were tested orally were inactive.

The 2-quinolinyloxyalkylaminoethanetiiiosulfuric acids (Table 30) also proved to be an

active series of compounds when administered intraperitoneally. In this series a 3-carbon

spacer conferred the greatest activity although it should be noted that only one compound

with a 4-carbon spacer was tested. The p'ntyl ethers were, with ole exception, inactive. The

unsubstituted quinolyl analog with a propyl spacer was quite active in contrast to the corres-ponding pyridyl analog. Methyl substituents on the ring increased activity but there was no

evidence that the presence of halogen on the ring, unlike the corresponding pyridyl series,

was salutary. Attachment of the ether chain at the 4, 5 or 8 positions yielded ineffective com-

pounds; compare WR 106,156 with WR 36,955, WR 25,930 with WR 9463. The unsubsti-

tuted 1-isoquinolyl derivative, WR 117,932, isomeric with the active quinolyl derivative,

WR 106,156, was inactive. As with the pyridyl ethers, the quinolyl ethers were also ineffec-

tive when administered orally.

In contrast to the Bunte salts, the best of the thiols in the 2-pyridyl ether series showed

only moderate activity when administered intraperitonealy and even less activity when

680

administered orally (Table 3 1). Although data are limited it would appear that a spacer of at

least 5 carbons in the side chain is necessary before activity appears. Relatively fRw of the

2-quinolyloxyalkylaminoethanethiols were prepared and none with appropriate ring sub-

stituents or alkyl spacers so that comparisons cannot be made.

2-[ (3-Thiazolidinylalkyl)oxyj pyridines and Quinolines (Tables 32 and 33)

Blocking the aminoethanethiol moiety of the 2-pyridyl ethers by incorporation in a

thiazolidine gave a series of compounds with only moderate activity when administered intra-

peritoneally; they were comparable in activity in general to the corresponding thiols but less

active than the Bunte salts, with ALD50 's generally higher than either of these classes

(Table 32). The outstanding characteristic of the class was the almost universal activity of the

compounds when administered orally and the remarkably high activity of certain of the

compounds. Although the oral doses of the compounds tested were larger in terms of mg/kg

than were the parenteral, they were approximately comparable to the latter when related to

the ALD5 0. The series exhibited oral activity over a range of spacers from 3 to 7 (n = 3-7);

the 5-halo-2-pyridyl ethers with spacers of 5 and 6 carbons showed the greatest oral activity.

In contrast to the pyridyl series, blocking the aminoethanethiol moiety as a thiazolidine in

the 2-quinolyloxyalkyl derivatives yielded a series of compounds which, for the most part

was inactive, and in which the best representatives showed only moderate activity regardless

of the route of administration (Table 33).

2-f (3-Thiazolidinylalkyl)thio] pyridines (Table 34)

The phenomenon of the good oral activity shown by the pyridyl ethers when the

aminoethanethiol moiety was incorporated in a thiazolidine was also apparent in the cor-

responding thio ethers, i.e., the 2-[(3-thiazolidinylalkyl)thioJ pyridines. Syntheses were con-

fired to the halopyridyl derivatives because of the concentration of activity in similarly

substituted pyridyl ethers. In the series of pyridyl thio ethers the greatest activity was ob-

tained with an alkyl spacer of 5-7 carbons (n = 5-7) when the compounds were administered

intraperitoneally (Table 34). The most effective range of spacers appeared to be somewhat

greater with oral administration (n = 5-8) (Table 34). It is also apparent that, in a number of

cases, the oral activity of the compound surpassed the parenteral at equal fractions of the

respective ALD 50 's. Relatively few of the corresponding quinolylthio ethers were synthesized

so that comparisons cannot be made. However, it is of interest that the only activity un-

covered in the latter quinoline derivatives was in those compounds in which the quinoline

ring was unsubstituted.

681

3-[ (Alkylthio)alkyll thiazolidines (Table 35)

A series of 3-[(alkylthio)alkyllthiazolidines (Table 35) were synthesized in which m

and n were varied. The degree of activity of the compounds when administered intraperito-

neally or orally was only moderate and variable depending upon the size of m and n. The best

activity in general, was shown by those compounds in which m + n = 9, 10 or 11, although

there were exceptions to this conclusion when m or n < 4. The noteworthy feature of the

series is the fact that any activity shown when administered intraperitoneally generally

carried over when the compounds were administered orally. The best compounds in the series

when administered orally were WR 157,311 and WR 134,783. The contribution of the sulfur

interruption of the chain is impossible to ascertain since an insufficient number of the simple

3-alkylthiazolidines were synthesized and tested. Data for the compound 3-octyithiazolidine,

WR 2949, are: ALD50 , IP, 150 mg/kg; 50 mg/kg dose IP rated +, t; ALD50 , P0, 700 mg/kg,

300 mg/kg dose PO rated +, +, -. For 3-decylthiazolidine, WR 2950, the data are: ALD5 0 , IP

75 mg/kg, 50 mg/kg dose IP rated +(T), +,0; ALD5 0 , PO, 550 mg/kg, 100 mg dose rated +.

The activity of these two 3-alkylthiazolidines, both intraperitoneally and orally, suggests that

the introduction of sulfur in the chain makes little difference. The oral activity of WR 2949

and WR 2950 stands in contrast to the lack of oral activity of the corresponding derivatives

when the sulfur of the aminoethanethiol moiety is present as the thiol itself (see below) or

blocked as the thiosulfate, although the latter compounds were highly effective intraperito-

neally. Oxygen analogs of the sulfur interrupted chains were not explored to any appreciable

extent. The oxygen analog of the very active WR 134,783, (Table 35), viz., WR 158,494, was

appreciably less 'active, both IP and PO, than WR 134,783.

Thus, as just discussed, the blocking of a thiol by incorp-nration of the aminoethane-

thiol moiety in a thiazolidine can, in certain series, result in active compounds when the com-

pounds are administered intraperitoneally and the activity can carry over, and sometimes beenhanced, when the compounds are administered orally. The octyl homolog, CH3 (CH 2 )7-

NHCH 2CH2 SH, WR 230, is about twice as toxic as the corresponding 3-(n-octyl)thiazolidine,

WR 2949, by intraperitoneal administration, but no more acti'e. Orally the thiol is 3-4 times

as toxic as the thiazolidine and is inactive; the thiazolidine, in contrast, has excefient activity.

The same type of relationship can be seen when comparing the n-decyl-thiol and -thiazolidine

analogs, WR 228 and WR 2950 respectively. Unfortunately the thiazolidines corresponing

to thiols with other good N-substituents, e.g., WR 2529, WR 2753, WR 2347 and WR IC65

were not synthesized but their synthesis and testing is certainly indicated. In investigating

682

new compounds it would be worth the effort to synthesize and test the corresponding thi-

azolidine if the thiol or a derivative with a blocked thiol proved to have appreciable intraperi-

toneal activity, regardless of its oral activity.

Aminoalkylaminoethanethiols and Derivatives (Tables 36 and 37)

Data from the testing of N-substituted derivatives of the amninoalkylaminoethanethiols

and -phosphorothioates [R1 R2 N(CH2 )nNHCH2CH 2 SY, Y = H, P0 3 H2 ] are shown in

Tables 36 and 37. The synthesis of such derivatives was confined mostly to the thiols (Y = H)

and the phosphorothioates (Y = P0 3 H2); relatively few of the corresponding disulfides

[Y = SCH2 CH2 NH(CH2)nNRiR 2 ] were s'inthesized and none showed remarkable activity.

Not nearly as many thiosulfuric acids were synthesized as were the thiols and phosphoro-

thioates; those thiosulfuric acids that were synthesized were less toxic than the thiols but

were uniformly inactive by intraperitoneal administration, even those corresponding to the

very active phosphorothioate congeners. They were not tested by oral administration and

have not been tabulated. Compounds in which the distal nitrogen is incorporated in a hetero-

cycle were essentially devoid of activity, regardless of the type of sulfur blocking, and have

been omitted from Tables 36 and 37. Most of the other derivatives where R1 is an alkyl

group substituted with such groups as hydroxy, polyhydroxy, amino, hetero, alkyloxy, alkyl-

thio, cyano, carboalkoxy and aryl are included in the table despite the -fact that such inclu-

sion makes the table replete with negative data. However, the fact that the best compounds in

this class were as good or better than any that emerged from the program makes the scope of

the structural types investigated and the comparison of structures the more important and

interesting, and justifies the plethora of negative data.

The thiols, RIR 2N(CH 2 )nNHCH 2CH 2 SY, (Y = H), (Table 36), were, as a class, less

active than the phosv~horothioates (Y = P0 3 H2 ), (Table 37), and had lower ALD50 s. Substi-

tution of alkyl groups larger than methyl (RI>CH3 ) on the distal N of the thiols abolished

activity and the best activity was seen when this N was unsubstituted. Alicyclic or terpenoidgroups on the distal N also abolished activity. Activity peaked when the nitrogen atoms were

separated by a chain of 3 carbon atoms (n = 3). 7Te number of thiols tested orally was

limited but, for those tested, oral activity was consistently lower than intraperitoneal ac-

tivity. The introduction of a hydroxyl group on the terminal ethyl group of the thiols

WR 6364 and WR 6365, (Table 36), decreased toxicity so that activity was evident in these

derivatives, WR 1751 and WR 2153, when tested at the higher tolerated doses. Based upon a

limited number of examp!,'s, the introduction of hydroxyl substituents on R1 when R! is

larger than ethyl (R1>C 2 1-h5) had little or no effect with respect to activity. Branching on a

A9R3

3-carbon chain separating the nitrogens, WR 156,788 and WR 157,529, resulted in the reten-

tion of appreciable activity but the introduction of a hydroxyl on this chain, WR 1783,

abolished activity.

The aminoalkylaminoethylphosphorothioates, (Table 37), as a class, include the most

active and most promising of the antiradiation agents synthesized. This class of compounds

was more active and had higher ALD 50 s than the corresponding class of thiols. Highest ac-

tivity was obtained when the distal nitrogen is unsubstituted or has only a methyl substitu-

tion; unlike the congeneric thiols, some activity was retained with alkyl groups slightly larger

than methyl. Large hydrocarbon moieties such as cycloalkyl or terpenoid substituted on the

distal N abolished activity. Peak activity, as with the thiols, was seen when there is a chain of

3 carbons between the nitrogen atoms (n = 3) but the base of activity was broader and the

peak was not nearly as well defined as in the case of the thiols. Good activity was retained

when the 3-carbon connecting chain between the nitrogen atoms is branched or when, in

contrast to the thiols, it is hydroxylated (WR 151,325). Replacement of the terminal amino

group with a guanidino group also resulted in active, but somewhat more toxic, compounds,

so that the therapeutic index seems unfavorable. Only a few of this type were made. Al-

though the best compounds of this class showed activity when administered orally, the degree

of activity was much less than when administered intraperitoneally, suggesting limited

absorption.

Aminoalkylamino•propanethiols and Derivatives (Tables 38 and 39)

Derivatives of the aminoalkylaminopropanethiols, RIR 2 NH(CH 2 )nNHCH 2CH 2-

CH 2SY, were not extensively investigated. For the most part, synthetic efforts were confined

to the thiols (Y = H) (Table 38) and the phosphorothioates (Y = P0 3H2 ) (Table 39). The

latter derivatives, unlike the simple derivatives of aminopropanethiols, showed excellent intra-

peritoneal activity when n = 2 or 3, R = H or CH3 , and Y = P0 3 1H2 (Table 39) and also when

n = 3, R = CH 3 , and Y = H (Table 38). When administered orally the activity of these same

compounds was less than when administered intraperitoneally, but was still quite good. Un-

fortunately, a direct comparison of several of the most active phosphorothioates with the

corresponding thiols is not possible. It is interesting that the corresponding guanidino deriva-

tive, WR 190,222, (Table 39), was also very active when administered intraperitoneally but

not when administered orally. Extension of the length of the chain connecting the nitrogens

beyon - carbons, i.e., n > 3, in the phosphorothioates abolished activity and the same was

true for the derivatives of 2-hydroxy-3-aminopropylphosphorothioate, R1 R2N(CH 2 )n"

NHCH 2CHOHCH 2SPO 3H2 . The latter compeund when R1 = R2 = H and n = 3

b684

(WR 142,489) is quite active by Intraperitoneal administration but inactive by oral adminis-

tration; this is in contrast to corresponding deshydroxy phosphorothioate, WR 44,923, which

retains good oral activity. The amninoalkylaminopropanephosphorothloates may deserve ad-

ditional attention.

It would appear, therefore, that the activities of the most active phosphorothioates in

the ethyl or propyl series were comparable, Le., in the series RNH(CH 2 )nNH(CH 2 )mSPO 3H2

when R = H or CH3 and n = 2, 3 or CH 2CHOHCH 2 , the activity of compounds where m = 2

was approximatr'W the same as those where m = 3.

N,N'-bridged-aminoethanethiols and Derivatives

When two aminoethanethiol molecules were joined through their respective nitrogen

atoms by a variety of bridges, the resulting compounds, with few exceptions, were inactive

and are not tabulated. Thus only two compounds in a series of N,N'-polymethylene-

bridged 2-aminoethanet',iols, HSCH2CH 2 NH(CH2 )nNHCH 2CH2SH, n = 2-12 (the heptylene-

bridged homolog, n = 7, was not synthesized) showed even moderate activity, vi7., those in

which n = 3 and 4, WR 2665 and WR 2209, respectively; hydroxylation of these bridges,

WR 1901 and WR 342, reduced but did not abolish activity. Compounds with other brid?es

such as 1,4-xylylede, butenylene, branched alkylene, polyether and hydroxyether were in-

effective. Although aU of the corresponding thiosulfuric acids, on a one-to-one basis were not

synthesized, there was a good representation and none showed any aztivity, including the two

that showed activity as thiols. Synthesis of the corresponding bridged phosphor,)thioates was

confined principally to those compounds with alkylene bridges. Intemstingly, the two bridges

that conferred a'ltivity in the thiol series were the same ones that appeared in the active phos-

phorothioates, viz., n = 3 and 4, WP. 3694 and WIP. 4431. These phosphorothioates were,

however, considerably more active than the corresponding thiols. As in the thiol series, the

analog with a hydroxypropylene brilge, WR 179,212, was also active but less so than the

analog with an unsubstituted bridge. The above comparisons again point tc the validity of the

generaLization that, in a given series of highly polar, water-soluble compounds, the phos-

phorothioates are usually the most active and the :hiosulfuric acids the least, with the thiols

occupying an intermediate position; toxicities usually follow the reverse order.

N,N'-polymclylene-bridged 3-aminopropanethiol Derivatives

A series of N,N'-polymethyleiie-bridged 3-aminopropanethiosulfuric acids, HO 3 SSCH2 -

CH2CH 2NH-(CH 2 )n-NHCi1 2CH 2 CH2SSO3 H, n = 3-10, were completely inactive. The

685

corresponding series of phosphorothioates, n = 2-5 and 7-10, were also completely inactive.

These negative data have not been tabulated. The corresponding thiols were not synthesized.

Mercaptoacetamidines and Derivatives (Tables 40-46)

The synthesis of the acetamidine derivatives was confined largely to those in which the

sulfur was blocked as a thiosulfuric acid or as a disulfide. The parent compounds, i.e., those

with no substitution on the nitrogen atom, were very active both by intraperitoneal and oral

administration regardless of the type of sulfur blocking (Table 40). Compared to the corres-

ponding aninoethyl analogs, the amidines are more efficient but also more toxic.

The simple N-alkylamidine derivatives were synthesized only as the thiosulfuric acids

(Table 41). There was a smattering of activity but this was generally of a low order. Com-

pound WR 166,823 was the most active of this group. The n-nonyl and n-decyl derivatives,

WR 2706 and WR 2608 respectively, were quite toxic. Introduction of a hydroxyl group on

the short chain analogs brought about no significant improvement.

The synthesis of N-aryl-, N-arylalkyl- and N-substituted-arylalkylarnidine derivatives

was also, almost exclusively, confined to the thiosulfuric acids (Table 42). A number of these

thiosulfuric acids showed activity with intraperitoneal administration ranging from poor to

fair but none of the compounds was outstanding. Those that were tested orally were inactive.The best compound was the N-(2-naphthyl) derivative as the disulfide, WR 199,737.

A small number of N-phenoxyalkyl- and N-phenalkyloxyalkylamidine derivatives,

along with some thio analogs, were synthesized, almost exclusively in the form of thiosulfuric

acids (Table 43). Several of these compounds exhibited good activity when administered in-

traperitoneally but were definitely less active administered orally. Thus the interruption of

the alkyl chain in the N-phenalkyl derivatives by oxygen or sulfur decreased toxicity com-

pared to the compounds with uninterrupted chains of equivalent length, e.g., WR 37,720 and

WR 60,237, (Table 43), compared to WR 3856, (Table 42), etc.; it would be of interest to

synthesize and test a few 2-naphthyloxyalkyl analogs. The pronourced increase in activity

brought about by the introduction of a methyl group on the phenyl ring, WR 8312 vsWR 32,379 is also noteworthy.

Synthesis of the N-cycloalkyl- and N-cycloalkylalkylamidine derivatives was also con-

fined mostly to the thiosulfuric acids and disulfides (Tables 44 and 45); the few thiols and

phosphorothioates that were synthesized are included in Tables 44 and 45 respectively. When

the compoLnds were administered intraperitoneally, fair to good activity was generally ob-

tained with both the disulfides and thiosulfuric acids. When administered orally the disulfides

were, as a rule, more active and more efficient. There seemed to be no discernible trend in

686

activity as a function of ring size or chain length. Most of the compounds had a high ALDSO

(PO)/ALDs(IP) ratio.The N-(l-adamantyl-) and N-(l-adamantylalkyl)-amidine derivatives, as disulfides

(Table 45), were characterized by low intraperitoneal ALD5 0 's and high ALD 5 0 (PO)/ALD5 0

(IP) ratios. Although they are, as a class, inherently active, as shown by their oral effective-

ness, no intraperitoneal activity was evident when the alkyl chain was longer than 2 carbon

atoms because of the necessity of testing at such low drug doses. The relatively high oral

ALD5 0 's may indicate limited absorption. In general, as a class, the compounds showed fair

to good oral activity although toxicity, as evidenced by early deaths, was prevalent. The cor-

responding thiosulfuric acids were also marked by a high ALDS0 (PO)/ALDS0 (IP) ratio. With

the exception of the parent N-(l-damantyl) and N-(l-adamantyl)methyl derivatives there

was little or no activity when the thiosulfates were administered intraperitoneally' and, with

one exception, WR 201,730, no activity when they were given orally, even though some of

the doses administered were quite large. Only a few of the 2-adamantyl isomers were synthe-

sized; as disulfides they were at least as active and possibly more active than their correspond-

ing I-adamantyl isomers both by intraperitoneal and oral administration. The limited data

also suggest that the 2-adamantyl isomers, as thiosulfuric acids, may be superior to the

l-adamantyl isomers when administered intraperitoneally; however, when delivered orally

they are inactive. As with the I-adarnantyl durivatives, the 2-adamantyl derivates also show "

a marked difference between the oral and intraperitoneal ALD5 0 's. In the few compounds

that were made with a sulfur-interrupted alkyl chain (Table 45), the activity of the disulfides

was at least equal to the corresponding analog with a non-interrupted chain both by the oral

and intraperitoneal routes of administration. A limited number of derivatives with oxygen-

interrupted chains as well as sulfur-interrupted were synthesized as ihiosulfuric acids. These

compounds generally had higher ALD 5 0 's than the compounds with uninterrupted chains of

equivalent length. Some of these had fair to good activity intraperitoneally but showed little

or no activity orally, as did their counterparts with non-interrupted chains. The amidine de-

rivatives containing N-terpcnoid moieties showed fair to gcad activity in both the disulfide

and thiosulfuric acid series when administered intraperitoneally (Tables 44 and 45). In the

case of the disulfides the activity carried over to oral administration; however, with the ex-

ception of the 2-bomyl analog, WR 92,973, there was little or no activity when the Bunte

salts were given orally.

Unlike the simple, unsubstituted aminoalkylthiols and thio derivatives, in which the

activity is essentially abolished if the alkyl chain connecting the N and S 3toms is extendedbeyond 2 carbon atoms, the amidines with longer chairs retain appreciable activity when

687

the compound is administered either intraperitoneally or orally (Table 46). The higher homo-

logs are less efficient than the lower on a mg/kg basis but the ALDS0 's am appreciably higher.

The synthesis of N-heterocyclic alkyl amidine derivatives was confined largely to the

thiosulfuric acids; the alkyl chains joining the heterocycle to the amidine moiety varied from

I to 3 carbons in length. In general, these compounds were disappointing and not tabulated.

Included An the compounds tested were the following heterocyclic moieties: 2-furyimethyl

and -ethyl; 2-tetrahydrofurylmethyl; 2-thienylmethyl and -ethyl; 2-, 3- and 4-pyridylmethyl

and 2- and 4-pyridylethyl, 2-benzimidazolylethyl, 3-indolylethyl and -propyl and 2-imid-azolldinone-2-yl ethyl. All of the pyridyl analogs were inactive as were the 2-furylmethyl, the

2-tetrahydrofurylethyl, the 3-indolylpropyl and the 24-midazolidinone-2-yl ethyl analogs.

The other compounds were active at the + level only at the highest tested doses. The bestcompound of the group was the 3-indolylethyl analog, WR 33,762. The 2-benzimidazolyl-

ethyl analog showed comparable activity as the thiosulfuric acid, thiol or phosphorothioate.

Guanidinoalkylthiols and Derivatives

The guanidinoalkylthiol derivatives, RNHC(=NH)N(RIXCH 2 )nSY, where Y = H, SO 3H,

or S(CH2)nN(RI )C(=NH)NHR, showed little or no activity and, as a class, were uninteresting

and not tabulated. Simple phosphorothioates were not prepared. All of the parent com-

pounds, I.e., R = RI = H, n = 2 or 3, and Y = H, SO3 H or S(CH2 )nN(RI)C(=NH)NHR, with

the exception of the guanidinopropyl disulfide, were active only at the highest drug doseadministered. When R or R I was alkyl the activity was reduced or abolished. It is interesting

that tie parent compounds H2NC(=NH)NH(CH 2 )nSH, n = 2 or 3, (WR 1574 and WR 2022respectively) which are generally regarded as the biologically active forms, respectively, of

the isothiuroniWum compounds H2N(CH2 )nSC(=NH)NH (AET, n = 2, WR 298), (APT, n = 3,

WR 215), were much less active thL. the latter compounds. The thiocarbonates correspond-

ing to the parent thiols, I.e., R = RI=H, n = 2 or 3 and Y = C(=S)SH (WR 783 and WR 1479

respectively) were also active, but no more so than the parents.

No-nitrogen Thiols and Derivatives (Table 47)

Thiols, or derivatives, which contain no amino group in the molecule, had shown little

or no activity in animals as a class and, therefore, had not been pursued in the antiradiation

Crug development program. In the course of the synthetic program, however, a small numberof such compounds became available and some showed activity comparable to the amino-thiols (Table 47). WR 168,643, a bis-sodium sulfinate trisulfide, was outstanding, both when

administered intraperitoneally or orally. Compounds that contain a thiol group or thiol

688

dertvative that can be bioactvated but contain no amino function would smen to hive great

theoretical importance with repect to mode of action. Since this ares has been little investi-

gated it would be worthy of further investigation.

689

TABLE 1

3- (2-MercaptoethylaminLo)propioaaide and Derivatives.Effect of Varying the Thlol-Blocking Group.

WR NO. STRUCTURE ALD5 d3 DOSE SURVIVALa mol/kg a aol/kg z

2529 U2 NCOCH2 CH2 NHCR2 CH2 SH 6.75 6.07 1003.03 901.52 701.18 0

139245 (B2MCOC"2C2MCRCR2- 2 2.12 1.70 730.85 13

2981 H2?COC 2 (C 2 NHC(L CH 2 SS03 H 5.26 3.50 531.75 7

6458 a2 NCOC H2 N cY 2 c2 ,SPO3-- 0.570 0.219 00.110

691

'_ -*,; : • -.• --- 2-- - - e-- -L t - -• "- 2- _V . . . . : .- _•-- -£- -- --- _-- - - -__-T . • - • -7 - -- --: /- T

TABLI 2

2-(3-Aaiuopropylaalno)ethanethiol and Derivatives.Effect of Varying the Thiol-Blocklng Group.

WR NO. STRUCTURE AL* 50 DOSE SURVIVALSmolk a mol/kg %

1065 H2(CH2) 3 WHC 2CH2SH 1.68 1.12 85

0.56 0

33278 ["Y' (c" 2 ) 3!McR 2c" 2 S-] 2 0.52 0.24 0

9720 H?2(CH SS0, 3.50 2.33 01.17 0

2721 H2 N(CH2 ) 3 1CH2 CH2SPO3H2 4.76 2.80 1001.40 1000.70 400.35 20

692

TABLE 3

n-Decylaanioethanethiol and Derivatives.

Effect of Varying the Thiol-Blocking Group.

WR NO. STRUCTURE ALDso DOSE SURVIVALa mol/kg m mol/kg 2

228 CH3 (CH2 ) 9 NHCH2 CH2 SH 0.299 0.115 800.058 20

1607 CH3 (CH 2 )9NHCK2 CH2SSO3 H 0.0504 0.017 1000.008 40

2294 CH 3 (CH 2 ) 9 NHCH2 CH2 SPO3H2 0.336 0.168 670.084 13

159241 CH3 (CH2 9 NHCH2CH2 SSCH2 CH2NHR(CH2 9C CH3 0.053 0.0462 2020.0231 0

693

•,• •, " . .•, 7° -•• ,• .•.•. • --. -a a _ <•: • ' ... •,-• - .

TrABLZ 4

2-Aminoalkylthiole

111H2NCCH2 SH

R2

ALD50 Drug Dose

UR NO. R1 R2 m/kg g/kg Rating

347 H H 300 150 +f+,0

186 CH3 H 300 125 +,0

339 CH3 CH3 350 200 +(T),

43 C2A 5 H >300 200 0(T),+,0

621 CH3CH2 CH2 H 140 100 +,+

2720 CH3 CH2 CH2 CH3 150 100 0

651 (Ce: 3 ) 2 CH H 160 t50 +,0

3349 -(CH 2 ) 4 - 250 75 0

2648 -(CH 2 ) 5 - 150 100 0

781 CH3 (CH2 ) 5 H 180 100 0

694

TABLE 5

2-Aminoalkylthiosulfuric Acids

R,

H2 NLCH2 SSO 3 H

ALD Drug 1Dose .Rating

WR NO. Rl !2u"p n/kg Rtn

361 H H 625 -350 +,+

1484 CR3 H 450 350 +

1488 CH3 CH3 800 600 +

182619 C2 5 H 600 0(T),+,0

2108 C2H5 CH3 700 300 0

1903 CH3 (CH2 ) 2 (DL) H 325 125 0

1904 CH3 (CH2 ) 2 (L) H 250 125 0

2085 CH3 (CH2 ) 2 (D) H 250 150 0

2176 CH3 (CH2 ) 2 CH3 300 150 0

4619 -lGH3 ) 2CH H 500 150 +10

2293 (CH 3 ) 2CH CH3 >400 150 0

1663 CH3 (CH2 ) 3 H 175 75 0

2177 CH3 (CH2 ) 3 CH3 300 200 O(T),0

1661 (CH3 ) 2CHCH2 H 200 150 0

2178 (CH3 ) 2CHCH2 CH3 240 150 0(T),0

1662 CH3 CH2CH(CH3 ) H 250 150 O(T),O

2649 -(CH 2 ) 4 - 800 300 +,+

2579 -(C1,1 2 ) 5 - 300 200 +,0

2381 CH3 (CH2 ) 5 CH3 180 100 0

1112 C6 HACH 2 H 250 100 0

695

TABLE 6

2-Am.inoalkylphouphorothioates

H2" jCH2 SP0 3 H2

R2

ALD5s Drug Dose

IJR NO. ___ wta/ka ag/kg Ratina

638 H H 525 400 +

4468 CH3 H 700 400 +,0

1490 CH3 CH3 750 600 +

4470 C2 H5 H 320 180 0

1961 CH3 CH2 CH2 H 375 250 0(T),±

5137 (CH3 ) 2 CH H 600 300 +,+

2378 (CH3 ) 2 CdCH2 H 250 100 0

3311 -(CH 2 ) 5 - 300 200 +

2819 CH3 CH2 CH2 CH3 >400 400 O(T),0

696

T*BLE 7

2-Mercaptoalkyiamines

.1H2NCH2cSH

R2ALD5 0 Drug Dose

WR NO. R R__k rn/kg Ratin

347 H H 300 150

166 CH3 (DL) H 425 300 ÷(T)_,,

2452 CH3 (D) H 400 200 +,0

2470 CH3 (L) H 600 200 +,0

1553 CH3 CH3 300 100 C(T),O

780 C2 H5 H 400 200

2726 C2H5 CH3 225 100 0

1554 CH3CH 2CH2 H 174 75 0

1568 CH3(CH2)3 H 120 50 0

1569 CH3(CH2)4 H 88 50

847 CH3 (CH2 ) 5 H 75 50 0

1696 CH3 (CH2 )6 H >120 60 0

2127 -(CH 2 ) 3 - 225 100 0

2086 -(CH2)4- 138 75 0

1987 -(CH 2 ) 5 - 70 30 0

2088 -(CH2)6- 100 40 0

2123 3-cyclohexenyl H 38 25 0

633 C6 H5 H 125 75 0(T),O

697

TABLE 8

2-Thiosultatoalkylamines

RIIH2NCHI2CHSSO 3 H

ALD Drug Dose

WR NO. R m_/n mg/kg Rating

361 H 625 350 +1+

2516 CHl3 >800 800 O(T),O

1036 C2 H5 500 350 +,0

1090 CH3 CH2CH2 188 150 0

1081 CH3 (CH2 ) 3 150 100 0

1144 CH3 (CH2 ) 4 150 125 0

1250 CH3 (CH2 ) 7 300 100 0

1734 C6H11 150 100 0

769 C6H5 --- 125 +,0

1446 C6 H5 CH2 88 50 0

698

TABLE 9

2-Aminoethanethiols. Effect of Functionalized Substituents.

H2 N-I-CH2 Sh

R2

ALDo 0 Drug DoseWR No. R, -2 Mg/K mg/kg Rating

2082 CH2SH H 13 8 0

2694 CH2S ! COOH 180 100 +,+

985 CH2COOH H 750 200 0

2389 CP2OH CH2OH 4000 1000 +9+,o

1996 CH2CH2OH H 800 500 +,0

4116 CH2SH CH2OH 30 5 0

1621 CH2 SH CH3 15 7.5 0

2704 CH2 CH 2 SH H 70 40 0

1076 COOC2 H5 H 1780 593 0

1265 CH2 SE C2 H5 18 10 0

2994 CH2OH C2H5 >800 750 0(r),0

193702 H2 N(CH2 ) 4 H 88 50 +,+,+,+

1986a HOCH 2 H 1200 800 0

2917a HO1 2 HOCHI 1800 1200 3

2717a HO3SSCH2 h >500 460 )(T)

a The corresponding thiosulfuric acid.

699

+1+0;0 0 0 4 +'-

0 0 0 0 0 0 0-i t 0 0 0 0 0n 0

C).~ 0 0 ui itn

LM oao 0 0 0 0% 0 0

AA A

+1I +1 +1+I + +

-~ t' 0 00

4-4 M 4-1a0s. 0 <

0 0- 0 M L

0) 00 01 t 0 0 0 0? 0114 4

00 0D 0 0 0 D~ in 0$4 tew 0 000 in 0 0 0 -.7 0 ~I c'0 Ný 0 , I ) Go 0 1 r

0

0~~~1 =4 0(A 0 0 ) t

CC4

't-4

r-4 "4 en 0% IT +N e lON N .-h 'T .. % r

C C' C' ý Cý .4 -.

VN r ON rý o o c

700

TABLE 11

Alkylaminoethanethiols aud -thiosulfates

RNHCH2CH2SZ

R Z a H Z - SO3H

WR NO. ALD 0 Drug Dose Rating WR NO. AfLD 50 Drug Dose Ratingmg/kg mg/kg mg/kg mg/kg

H 347 300 150 +,+,0 361 625 350 +,+

CH3 2113 300 200 +,0 258 350 300 +,+

C2H5 889 350 150 0 1095 525 300 +

CH3(C"2)2 1426 125 75 0 1033 350 225

CH3(CH2)3 224 350 60 0 2244 300 200 0

CH3 (CH2 ) 4 2316 75 30 0 2341 200 50 0

CH 3 (CH 2 ) 5 234 50 10 0 2137 100 75 0

CH3 (CH2 )6 1548 75 30 0 2078 125 75 0

CH3 (CH2 7 230 75 40 +,0 1618 125 30 +(T),÷

CH3 (CH2 ) 8 1547 125 25 + 1818 40 5 +,+

CH3(CH2)9 228 43 25 +,+ 1607 13 5 +,+

CH3(CH2)10 1549 45 30 +(T) 2111 8 5 0

CH3 (CH2)11 2297 25 15 0 2080 10 5 0

CHl3 (CHl2 ) 12 2059 35 25 0 2236 10 5 +,0

CH3 (CH2 ) 1 3 2334 40 25 O(T),0 2281 10 5 +

CH3 (CH2 ) 1 4 2084 60 25 0 2345 40 30 0

CH3(CH2)15 1710 150 120 0 2412 150 40 0

CH3(CH2)16 2047 100 50 O(T) 2356 200 100 0

CH3 (CH2)17 1711 400 200 0 2362 400 250 0

701

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703

TABLE 13

Phenalkylaminoethanethiols

A,••--CH2)n-NHCH2CHI2SH

ALD) 0 Drug DoseWR No. A n Mg/ai mg/kg Rating

1891 H -- >500 300 0

2423 4-F -- 600 200 0

4118 4-OC2H5 - 750 250 0

217 H CH2 100 90 _(T),O

1789 4-CH2 OH CH2 250 100 0

1245 4-OCH3 CH2 110 90 0(T)

3233 H (CH2 ) 2 80 40 +,0

2302 3,4-(OCH3 ) 2 (CH2 ) 2 90 75 0

2298 H (CH2 ) 3 75 25 0

2308 H CH2 CH(CH3 ) 90 50 0

2299 H CM(C 2 H5 ) 80 25 0

2397 H (CH2 ) 4 75 25 0

36956 4-OCH3 (CH 2 ) 4 70 40 0

704

TABLE 14

Phenalkylaminoethanethiosulfuric Acids

A • (CH 2 )n-NHCH 2 CH2 SSO3 H

ALD) 0 Drug DoseWR No. n A mg/kg Rating

3552 -- H >800 400 0

2230 CH2 H 250 150 O(T),0

4701 CH2 4-OCH3 180 100 0

2456 (CH 2 ) 2 H 150 50 0

2229 (CH2)3 H 125 50 +,0

3300 (012)3 2-OCH3 200 75 +(T),0

2144 (CH2 ) 3 3-OC13 300 50 0

4547 (CH2)3 4-OCH3 200 75 +,0

2754 (CH2)4 H 300 120 +0+,0

71462 (CH2)4 4-Br 43 32 0

3086 (CH2)4 4-CH3 15 5 0

3337 (CH2 ) 4 2,5-(CH3 ) 2 20 10 +,0

3340 (CH2 ) 4 2,4-(CH3 ) 2 38 15 +,0

3342 (CH2 ) 4 4-C2H 5 15 5 +,0

4102 (CH2 ) 4 2-OH 300 100 0

3050 (CH2)4 4-OCH3 175 100 +,+,+,+

4109 (CH2)4 3-OCH3 150 75 +,+,0

3338 (CH2 ) 4 3,4-(OCH3 ) 2 350 150 +,0

4103 (CH2 ) 4 4-OC2 H5 22 15 _+(T),

3611 (CH2 ) 4 4-C 6 H1 1 15 15 0(T),_

6138 CH(C 2Hs)CH2 3-OCHU2 100 40 +.,

705

TABLE 14

Phenalkylaninoethanethiosulfuric Acids

A •,- (CH2 ),-NHCH2 CH2 SS03H

ALD5 0 Drug Dose

WR No. n A mg /kg (s Ratinng

3552 -- H >800 400 0

2230 CH2 H 250 150 0(T),0

4701 C02 4-OCH3 180 100 0

2456 (CH2 ) 2 H 150 50 0

2229 (CH 2 ) 3 H 125 50 +,0

3300 (CH2 ) 3 2-OCR 3 200 75 +(T),0

2144 (CR2 ) 3 3-OCR 3 300 50 0

4547 (CR2 ) 3 4-OCR3 200 75 +,0

2754 (CH 2 ) 4 H 300 120 +,+,0

71462 (CH2 ) 4 4-Br 43 32 0

3086 (CR2 ) 4 4-CH3 15 5 0

3537 (C1 2 ) 4 2,5-(CH3 ) 2 20 10 +,0

3340 (CR2 ) 4 2,4-(CH3 ) 2 38 15 +,0

3342 (CR2 )4 4-C 2 H5 15 5 +,0

4102 (CR 2 ) 4 2-OH 300 100 0

3050 (CH 2 ) 4 4-OC 3 175 100 ,+,+,+_

4109 (CH 2 ) 4 3-OCH3 150 75 +,+,0

3338 (CR2 )4 3,4-(OCH3 ) 2 350 150 +,0

4103 (Cli 2 ) 4 4-0C2 H5 22 15 _(T),±

3611 (CH2 ) 4 4-C 6Hll 15 15 O(T),+

6138 CH(C 2 H)C02 3-OCR1 100 40 +,0

705

TABLE 15

Hydroxyalkylaninoethanet hiole

RNHCH2 CH2 SH

ALl)D0 Drug DoseWR NO. • •u/ .s/kg Rating

698 HOCH2 CH2 750 400 +,0

1119 HOCH 2 CH2CH2 750 500 +,0

727 CH 3 CHOHCH2 475 300 +,+

2112 L -HOCH 2 tHCH 3 450 300 +,0

2753 (HOCH 2 ) 2 CH 1200 600 +,+,0

1120 HOCH2 CHOHCH2 1300 1000 +,0

1191 HOCH2 (CH2)3 281 250 0

668 CH3CH2CHOHCH2 275 200 0

699 CH 3 CHOHCHCH 3 88 50 0

843 HOC(CH 3 ) 2 CH2 325 150 0

1104 HOCH2liBI&CH2 Cli 3 238 200 0

1780 HOCH2 1(CH3 ) 2 188 125 0

1788 (HOCH 2 ) 2 CCH 3 700 600 0

2846 HOCH 2 (CUOH)2CH 2 1700 1500 +(T) ,+

2347 HOCH 2 CHOHi&IiCH2OH 2000 1200 +,+,_.,

4123 (OCH 2 ) 2 C(OH)CH2 1650 1250 +(T),+,0

1616 (HOCH 2 ) 3 C 1300 800 +(T),+,0

2469 HOCH 2 (CH2 ) 4 1200 200 +,0

2816 CH 3 CH(CH3 )&CH 2 OH 200 90 0

2863 CH 3 (CH2 ) 2 &CH 22OH 140 100 0(T),0

2664 HOCH 2 (CH 2 ) 2 CHOHCH2 800 600 +9+,0

707

TABLE 15(Continued)

ALD5 0 Drug DoseWR No. R R mg/kg Rating

2003 CH3 CH 2 C(CH 2 OH) 2 625 375 0

3297 (CH 3 ) 2 C(OH)CH2 OHCH2 650 200 0(T),04611 CH3 (CH 2)2 CHOHCHORCH2 320 150 +,0

1103 CH3 (CH2 )2 C(CH3) (OH)CH 2 175 125 0

2854 CH3 (CH2 ) 3CCH 2OH 150 50 0

2465 CH3 (CH2 ) 2 CHOHC(CH3 ) 2 100 50 0

1190 CH3 (CH2 ) 5CHOHCH 2 83 50 0

1781 (CH3 ) 2 C((OH)(CH2 ) 3 CHCHl3 175 150 0

2855 CH3 (CH2 ) 5 CHCH 2 OH 75 25 0

3999 CH3 (CH2 ) 3 C(C 2 H5 ) (OH)CH2 125 25 0

4703a CH3 (CH 2 ) 4 (CHOH) 2 CH2 200 20 0

5025b CH3 (CH2 ) 4 (CHOH) 2 CH2 200 20 0

1895 CH 3(CH2 ) 7 CHOHCH 2 88 50 0

29005 HOCH 2CHOH(CH 2 ) 9 160 100 +,0

1898 CH3 (CH2 ) 9CHOMCH 2 88 50 0

a Racemate 1

b Racemate 2

708

TABLE 16

Hydroxyalkylaminoethanethiosulfuric Acids

RNHCH2 CH2 SSO3 H

ALD 5o Drug DoseWR NO. R tug/k ma/ka Rating

3124 HOCH2CH2 1200 800 +,0

3095 HOCH2CH2 CH2 700 800 O(T),0

2997 CH3 CHOHCH 2 600 400 0

2986 HOCH 2 CHOHCH2 1750 1000 +,0

3569 (HOCH2)2CH 1750 1250 +,+_,0

2905 HOCH2 CHOH&CH2OH 1500 1000 +(T),0

3273 HOCH 2CRHOHCHOHCH 2 1800 1600 +(T),0

3093 (CH3 ) 2 C(Ol)CHOHCH 2 1400 1000 +(T),o

2970 HOCH 2 (CE2 ) 6 550 300 0

2971 HOCH 2 (CH 2 ) 7 625 200 +,0

2865 CH3 (CH 2 ) 5 &HCH20H 140 80 +,0

2908 HOCH2(CH2)8 350 200 +,o

2907 HOCH 2 (CH2 ) 9 >200 100 0

2909 CH3 (C12 ) 7CHCH2 OH 25 5 0

3024 HOCH2 (CH2 )8 CHOHCH2 400 250 0

27748 HOCH 2CIIOH(CH2 ) 9 400 200 0

709

TABLE 17

Hydroxyalkylaminoethylphosphoro thioates

RNHCH2 CH2 SpO3 H2

ALDC Drug DoseWR NO. R 7L img/kg Rating

8186 HOCH2CH2 950 1200 +9,+9,+,O

8192 CH3CHOHCH2 1250 700++,

8187 HIOCH 2CHOHCH 2 2000 25') 0

27736 CH3CH2CH2(CHOH)2CH2 450 150+,

27077 (CH3)2CH(CHOH)2CH2 275 100+,

42597 (CH 3 CH2 )2 CHCHOHCH2 240 180 +T,,

25077 CH 3(CH 2)4 (CHOH) 2CH 2 300 100+,

36978 (CH3)3CCH2CH(C113)CHOHCH2 125 80+,,

52114 Cli3(CH2)4CHOHCH2CHOHCH2 1800 1000 0

710

TABLE 18

Hydroxyalkylaminoethyldisulf ides

RNIHCH 2 CH2 SSCH2CH2 NHR

ALD 0 Drug DoseWR NO. R MgR/g mg/kg Rating

3123 HOCH 2CH2 800 400 +,0

3097 HOCH 2CH2CH2 500 315 +,0

29563 HOCH.2CHOHCh 2 1250 800 S,S

3568 (HOCF 2 ) 2 CH 1250 800 +(T),+

39748 HOCH2 (CH2 ) 4 600 400 0

36951 HOCH2 (CH 2 ) 5 220 100 0

4853 Ci3 (CH2 ) 4CHOHCHOHCH 2 (rac. 1) 75 25 0

5027 C113 (CH 2 ) 4 CHOHCHOiCH2 (rac. 2) 75 25 0

30462 HOCr.2 CHOH(CH2 ) 9 175 80 0

3331 CH (CH 2) 7 CHOH) 2 (CH2 ) 8 133 50 0

3333 Uf3 (CH2 ) 5CHOH(CH 2 ) 11 133 80 0(T),0

711

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c n CO r- e ~( ' N - n

712'

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t4 , 0 m

to,

C.4 LA c.) C.

TABLE 20

Cycloalkyloxyarninoethanethiosulfuric Acids

R-0-(CH2 )n•qC- 2CH2 SSO3H

INTRAPERITONEAL DATA ORAL DATA

ALD5 0 Drug Dose ALD5 0 Drug DoseWR NO. R n mg/kg mg/kg mtig/g m__gp/k _ Rating

3069 (CH2):,Cd 3 150 50 0

4111 (CH2'K 4 150 75 0 --

2972 (CH2 ) 5 CH 4 150 75 4(T),O 1500 750 0

4444 (CH 2 ) 6 CH 4 150 75 +(T),O .--.

4446 (CH 2 )7 CH 4 250 100 +(T),+,+,0 - - -

4541 (CH 2 ) 4 CH 5 150 100 f-,0 1300 600 0

2973 (CH2)sCH 5 150 75 +(T),+,0 >800 600 +

4538 2-CH3C6 H1 0 5 75 30 +(T),+(T),O 1100 500 0

4781 1-1;3 C6 H1 0 5 150 25 +,+ 1000 800 0

4540 4-CH3 C6 H10 5 18 12 +,0 1300 600 0

138415 2-(CH3 ) 2CH-5-CH3 5 60 30 +,+P,,0 >900 600 0--C6H 9-

4542 (CH 2 ) 6 CH 5 35 25 +,0 - - -

4545 (CH2)4CH 6 200 50 +(T),4- 1800 1000 +

29C, (CH2)5Ch 6 150 20 +,0 - - -

4544 (CH 2 ) 5 CH 8 15 10 +(T),O ....

3610 (CH 2 ) 5 CHCH2 CH2 , 38 15 +,0 - - -

25331 (CH 2 ) 5 CHCH(C 2 H5 ) 4 96 60 +,+,0 >600 600 0

3567 (CH12 ) 5 CHCH2 5 18 12 +,P -

33716 (CH2)7 CH 5 180 50 +,+ -

714

TABLE 21

Phenoxyalkylaminoethanethiols

A"-(CH2 )nNHCH 2 CH2 SH

ALD5 0 Drug Dose

WR NO. A n / mgN/kg Rating

2628 H 2 100 50 +,0

3354a H 2 90 50 0

3293 4-(CH3 ) 3 C 2 150 100 +,0

3307 4-Cl 2 125 75 0

3583 H 3 88 50 +,0

6369a H 3 90 50 0

2654 2-C 2H50 3 90 50 0

33717 4-CH3 4 75 40 +,+

36160 2,5-(Cd3 ) 2 4 70 40 0

31893 2,6-(CH3 ) 2 4 75 50 +,+

38493 2,3,6-(CH3 ) 3 4 130 100 +(T)

36960 2-(CH3 ) 2 CH 4 90 50 0

3a897 2-CH3 5 100 5f +,+

33711 2-CH3 6 150 40 0

a. The phenylthio analog

715

TABLE 22

Phenoxyalkylaminoethanethiosulfuric Acids

A & 10- (CH2 )nNHICH 2CH2 SSO3 H

INTRAPERITONEAL DATA ORAL DATA

ALD5 0 Drug Dose ALD~o Drug DoseWR NO. A n mg/kg mg/kg Rajt/g mg/kg Rating

2146 H 2 175 100 0

4381a H 2 200 50 0

3071 3-Cl 2 150 100 +,0 -- --

3240 2-C2H50 2 150 100 0 --- -

4543b H 2 700 25 0 - - -

3237 H 3 150 50 0 - -

5146a H 3 175 75 +,0 --

3301 3-CH3 3 125 75 0 ----

5979 2-CH3 3 150 75 0

3305 H 4 >250 200 O(T),0(T) - -

3431a H 4 75 50 0 - - -

3087 2-CH3 4 150 50 +(T),+,+.O - - -

2941 3-CH3 4 175 50 +,0 1050 600 0

3121 4-CH3 4 35 25 +,0 1400 1000 +,0

3565 4-C 2 H5 4 40 5 0 - - -

33712 2-(CH3 ) 2 CH 4 320 250 O(T),+(T)

4537 4-C 6 HII 4 50 10 0 - - -

3830 4-CH3 0 4 200 90 +(T),+,O >2000 1000 0

3828 4-c 2H5 0 4 95 50 +(T),+ > 100 12.5 _(T),O

71-.• ...... .

TABLE 22

(Continued)

INTRAPERITONEAL DATA ORAL DATA

ALD50 Drug Dose ALD50 Drug DoseWR No. A n mg/kg ag/kg Rating mg/kg - mg/kg Rating

5981 4-Br 4 >150 50 O(T),O(T) - -

4106 4-Cl 4 175 75 +(T),± - - -

3819 3-Cl 4 150 100 +,+ >1250 1000 +

4792 2-Cl 4 150 50 +,+ >3200 1000 0

111489 3-(C 2H5 ) 2 N 4 175 50 +,+,0 > 900 600 0

4447 4-NO2 4 150 50 +,+ >2400 2000 0

3335 3-CF 3 4 45 30 + >1200 1200 0

4769 2,3-(CH3 ) 2 4 22 15 +(T),+,O - - -

3336 2,4-(CH3 ) 2 4 20 10 +,+ >1000 1000 O(T)

4805 2,5-(CH3 ) 2 4 40 30 +,+ >2000 1500 0

4788 2,6-(CH13) 2 4 250 100 +,+,+ >1500 1400 0

3343 3,4-(CH3)2 4 45 30 +,+ >1200 1000 0

124940 3-CH3 -4-(CH 3 ) 2 N 4 150 50 +,0 - --

75234 3-(CH3 ) 2 N-4-CH3 4 180 100 +(T),+,+ > 900 600 0

6137 3-CH3-4-CH 3S 4 187 50 +,+,0 - - -

150640 3-NI12-4-CH 3 4 150 100 0 >300 300 0

3122 2,4-C1 2 4 125 25 +f, >2000 2000 0(T),0

43899 2,4-1(CH3 ) 2 CH] 2 4 75 30 0 - - -

3832 2-CH30-4-C 2H5 4 125 75 +(T),+ >2400 800 +(T)

36958 2,3,6-(CH3 ) 3 4 >100 50 0 - - -

39750 2-C1-4-Br 4 75 50 0 - - -

40640 2-(CH3 ) 3 C 4 38 5 0 ...

3822 H 5 > 50 50 +(T),+,+,0 >2000 1000 0

717

TABLE 22(Continued)

INTRAPERITONEAL DATA ORAL DATA

ALD5 0 Drug Dose ALD 0 Drug DoseWR NO. A n mg/kg mg/ks Rating MR/ a/kg Rating

3826a H 5 300 50 + - - -

4546 2-CH3 5 200 70 +,+,+,+ >3200 200 0

136181 3-(CH3 ) 2 N-4-CH3 5 135 90 +(T),+,+,0 - -

3821 H 6 500 50 0 - - -

4777 2-CH3 6 150 50 +,+,+,0 >1500 1400 0

a. The phenylthio analogb. 2-Naphthyloxyethylazinoethanethiosulfuric acid

718

TABLE 23

Phenoxyalkylaminoethyldisulf ides

ALD5 0 Drug Dose

WR NO. A n :0/kg .a/kg Ratin&n

6368 H 3 120 50 0

5141a H 3 150 50 0

33895 4-CH3 4 430 320 O(T),+(T)

36159 2,5-(CH3 ) 3 4 45 15 0

33714 2,6-(CH3) 3 4 560 320 O(T),0

40644 2.3,6-(CH 3)3 4 56 30 +,0

43893 2-((CH3 ) 2 CH 4 10n 56 +,0

40643 4-CHl3 0 4 430 320 +,+

33896 2-CH3 6 74 56 O(T),+

a. The phenylthio analog

719

TABLE 24

3-(Phenoxyalkyl) thiazolidines

INTRAPERITONEAL DATA ORAL DATA

ALD5 0 Drug Dose ALD 0 Drug DoseWR NO. R n mg/kg mg/kg Rating mg/g Rating

34142 4-CHl3 4 175 50 + 50 +

39744 2-(CH3 ) 2 CH 4 75 50 0

117934 3-(C 2H5 ) 2 N 4 200 60 0 225 0

136180 3-(CH 3 ) 2 N-4-CH3 4 175 50 0 600 300 O(T),0

43901 3,5-[(C(3)2CHI]2 4 200 40 0 > 750 500 0

138410 3-Cl 4 200 90 +,0 650 300 +

138411 2-OCH3-4-C 2H5 4 135 70 +,0 500 150 0

145722 3-NO2-4-CH 3 4 175 50 0 550 300 +(T),0

42760 2,3,6-(CH3 ) 3 4 180 100 0

151332 2-CH3 -4-Br 4 85 40 0 450 400 0

38489 2-CH3 5 430 160 +(T),+ >1000 300 +

138418 2-(CH3 ) 2CH-4-CH3 5 300 150 +,o 900 500 0

136182 3-(CH3 ) 2N-4-CH3 5 175 50 0 400 200 +(T)

720

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TABLE 26

Cycloalkylalkylaminoethanethiols

R- (CH2 ) n-NICH2 CH2 SH

ALD0 Drug DoseWR NO. R n __/__ mg/kg Rating

2638 (CH2 ) 2CH 0 250 200 +(T) 0

227 (CH2)5CH 0 85 60 0

956 2-0l-C 6 HlO 0 200 100 0

2398 1-C 6H5-C66l 10 0 60 30 0

2392 4-(CH2 )5 CH-C 6 HIO 0 150 50 0

2391 (CH 2 ) 6 CH 0 70 45 0

2394 (CH2 ) 7 CH 0 175 25 0

74170 2-norbornyl 0 130 100 0

2468 (CH2 ) 1 1 CH 0 50 30 0

41245 2-bornyl . 0 74 56 +,0

51983 1-adamantyl 0 63 20 0

125697 2-adamantyl 0 75 30 0

2058 (CH 2 ) 2 CH 1 88 50 0

2641 (CH 2 ) 3 CH 1 80 50 0

2639 (CH 2 ) 5 CH 1 .80 30 .0

2307 2-norbornyl 1 90 40 0

3156 2-CH3-2- 1 .13 125 0norbornyl

142078 1-adamantyl 1 85 30 0

3155 2-norbornyl 2 70 30 0'

142075 1-adamantyl 2 50 25 +,0

2650 (CH2 ) 4 CH 3 75 25 1

31894 (CH 2 ) 5 CH 3 75 25 0

156784 1-adamantyl 3 > 60 60 (T),0

31896 (CH 2 ) 4 CHI 4 70 40 +,0

4808 (CH2)5CH 4 50 40 +,0

33715 3-CH3C6 HIo CH(C 2H5 )CH2 62 25 0

34140 2,4-(CH3 ) 2 C6 H9 4 40 15 +

TABLE 26(continued)

ALD Drug Dose

WR NO. R n mg/iR mg/kg Rating

39742 (CH2 ) 5 CH CH(CH3) (C2)3 75 50 0

36957 OR 2)4CH 6 75 40 S(T)

2576 (CH 2 ) 5 CH 6 75 30 +,0

727

TABLE 1'

Cycloalkylalkylaminoethyldieulf ides

(R- (CH 2 )n-NHCH2 CH 2S-] 2

ALD5 0 Drug DoseWP NO. R n mita mg/kg Rating

692 (Ch,) 5CH 0 92 70 0

43680 2-oornyl 0 180 100 0

148667 1-adamantyl 1 75 30 0

196267 4-H 2 NCH2 C6 H1 0 1. 60 30 0

3023 (CH2 ) 5 CH 4 22 15 +_,

33713 (CH2 ) 5 CH CH(C2 H )CH2 45 25 0

36952 02) 5CH CH(CH3)(CH 2)3 45 10 0

728

TABLE 28

Cyc] :a2.•. 4lkylaminoethylphosphorothioates

R-(C, 2 ) -NHCH 2 CH2 SPO3 H2

ALD50 Drug DoseWR No. R mg/kg mg/kg Rating

40335 2-bornyl 0 430 320 +,0

35979 1-adamantyl 0 240 80 +,+,0

125696 2-adamantyl 0 150 70 0

133567 (CH2 ) 1 1'-H 0 70 30 0

74171 2-nrobornyl 0 240 90

142076 1-adamantyl 2 70 35 +(T) ,

4481 4-CH3 -2(-O)C 6H8 C(CH3 ) 2 375 250 0

151321 1-adamantyl 3 115 70 +,0

159742 (CH2 ) 5 CH 4 45 11 0

117909 (cl 2)5 CH CH(C 2H5 ) CH2 125 30 0

4480 2(-0)C6H9 CH(n-C3H7) 88 25 0

75235 4-C 6HII-C 6 HI1 4 >1800 300 0

729

TABLE 29

2-Pyridyloxyalkylaminoethanethiosulfuric Acids

2AnN•• O 2 -CN 2 CH2 SSO3H

INTRAPERITONEAL DATA ORAL DATA

ALD 0 Drug Dose ALD Drug DoseWR NO. A mi Rsk mgt/kg Rating M&Mi mg/kg Rating

37679 H 2 125 0

104704 5-Cl 2 150 75 0(T),O

99590 5-Br 2 175 100 O(T),O

98080 H 3 195 100 0

80859 3-Cl 3 160 80 0

122961 5-Cl 3 150 90 +(T),+,0 800 400 0

54203 5-Br 3 125 80 +,+ > 900 500 0

91493 3-NO2 3 175 80 0

91489 5-NO2 3 180 90 +,0

80865 6-0C2 H5 3 105 60 0

108504 5-Cl 4 190 100 +,+,0 >1200 600 O(T),0

104695 5-Br 4 180 100 +,+,0 > 900 500 0

82422 5-Cl 5 225 150 +(T),+(T),+(T),+,O >1000 1000 0

138412 3,5-cl 2 5 175 50 +,+#+,0 900 450 +,+

99582 3-Br 5 170 90 +,+

43900 5-Br 5 90 50 +,+,0

50480 6-Br 5 140 100 0

99581 3,5-Br 2 5 160 50 +,+,+,0 >1200 800 0

99575 5-1 5 100 50 +,0

117931 5-CN 5 175 80 0

730

TABLE 29(continued)

INTRAPERITONEAL DATA ORAL DATA

AL)0 Drug Dose ALD5 0 Drug DoseWR NO. A / mg/kg Rating ma/kg mg/kS Rating

104696 5-WO2 5 150 80 +,+ >900 600 0

85565 4-CH3 5 185 100 0

94533 5-CH3 5 125 70 +,+,0 >900 600 0

106162 5-Cl 6 120 60 O(T),+,+ >800 600 0

91494 5-Br 6 225 50 0

124950 3,5-Br 2 6 250 15 +,0

145723 6-Br 7 50 20 0

146105 5-1 7 100 20 0

94531 5-Br 10 160 80 O(T),0

I

731

TABLE 30

2-Quinolyloxyalkylaminoethanethiosulfuric Acids

Ao •(CM2 ) nNHCHCH 2 SSO3 H

INTRAPERITONEAL DATA ORAL DATA

ALD• 0 Drug Dose ALD) Drug Dose

WR No. A n R/ mg/kg Rating mg/ mg/kg Rating

104700 4-CH3 2 280 140 0

122960 4-CH3,6-OCH'3 2 100 50 +(T),+,+,0

106156 H 3 220 100 +,+,+,0

2 5 9 3 0 a H 3 450 100 0

9463b H 3 125 100 0

122968 4-OCH3 3 175 80 +$+,0

54204 4-CH3 3 180 100 +,+,+9+ >900 400 0

134784 4-CF3 3 160 30 +,0

120769 4-CH3,8-C1 3 300 10 0

108502 4-CH3 ,6-C1 3 75 30 +,+ >600 600 0

111490 4-CH3 ,6-OCH 3 3 100 25 +,_

122970 4,6-(CH3 ) 2 3 125 70 +,+,+, >900 600 0

126456 4-C 3 H7 3 125 60 +,+,0 >600 400 0

104706 4-CH3 4 225 100 +,+,+,0 >750 500 0

111486 4-Cl 5 275 10 0

122959 4-OCH3 5 225 100 +,+ >900 600 0

42761 4-CH3 5 740 560 0

123953 4,6-(CH3 ) 2 5 115 30 0

132199 4-CF 3 5 250 5 0

111492 4-CH3 ,6-C1 5 175 70 0(T),O

732

TABLE 30

(Continued)

INTRAPERITONEAL DPI.A ORAL DATA

ALT)50 Drug Dose LD5 0 Drug DoseWR No. A n mgL/kg mg/kg P-£L mg/kg Rating

120768 4-C113 18-C1 5 325 20 0

124951 4-C3 K7 5 120 5 0

36955c 7-Cl 5 250 150 0

119dH 5 175 30 0

106157 4-CH3 6 90 15 0

a 5-Quinolyloxypropylaminoethanethiosulfuric acid.

b 8-Quinolyloxypropylaminoethanethiosulf uric acid.

c 7-Chloro-4-quinolyloxypentylamiaoethanethiosulfuric acid.

d 1-Isoquinolyloxypentylaminoethanethiosulfuric acid.

733

- - .- -;

TAPLE 31

2-Pyridyloxyalkylaainoethanethiolu

A41,O (CH 2) nlflCl20B2 Sl

INTRAPERITONEAL DATA ORAL DATA

ALDSO Drug Dose ALD) 0 Drug DoseIlk NO. A ni mgkg i/kg RatiRS =I u/kg Rating

26169 H 2 120 80 O(T),O

99586 5-Br 2 110 50 O(T),O

122961 5-Cl 3 87 40 0

54202 5-Br 3 150 50 0

111485 S-Cl 4 100 35 0 250 100 0

106155 5-Br 4 125 50 0

85563 5-cl 5 110 60 +,0 700 300 +(T)

159246 3,5-C12 5 130 70 +,0 510 250 O(T),O

104699 3-Br 5 125 50 0

42764 5-Br 5 240 90 +,0

99588 3,5-Br 2 5 150 80 0

99587 5-1 5 150 50 0,+ 400 150 0

91491 4-CU3 5 97 40 0

99579 5-CU3 5 80 45 0

106165 5-Cl 6 140 60 +,0 350 150 0

91495 5-Br 6 140 60 +,+ 350 200 +(T)

94536 5-Br 10 52 30 +_,

734

TABLE 32

Substituted 2- [(3-thiazolidinylalkyl)oxy]pyridines

A-o'(CH2)n--.fD

INTRAPERITONEAL DATA ORAL DATA

ALDSO Drug Dose ALD5o Drug DoseWR NO. A n L Mkx Rating ,a/kg ag/kg Rating

104701 5-Cl 2 150 75 O(T),O 400 200 0

99576 5-Br 2 150 80 O(T),O

122962 5-Cl 3 125 60 0 450 300 _(T),O

147954 5-1 3 175 80 0 >900 600 4,0

108505 5-Cl 4 275 120 +,0 750 600 +,+

104703 5-Br 4 250 100 +,0 600 250 +

148743 5-I 4 >300 100 +,0 >1000 400 +,0

40641 H 5 >200 50 0

85562 5-Cl 5 160 80 +,0 650 300 +9+

138413 3,5-C1 2 5 150 50 0 >900 450 +9+

99584 3-Br 5 280 100 0

43898 5-Br 5 240 150 +,+ 900 500 +(T),+,+

99583 3,5-Br 2 5 >320 200 0

94542 5-I 5 230 100 +,0 >900 600 +,+,+,0

132193 5-SCHl3 5 200 60 0 550 300 0

94538 5-CH3 5 190 70 +,0 700 375 +(T)

91496 5-Br 6 200 100 +,+ >525 300 +,+

126454 3,5-Br 2 6 274 130 0 800 200 0

108503 5-Cl 6 220 75 +P+ >600 300 +,+,+

735

TABLE 32(continued)

INTRAPERITONEAL DATA ORAL DATA

ALD50 Drug Dose ALDso Drug DoseWR NO. A n ! us/ka Rating !/k mR/kg Rating

132197 5-I 6 125 50 +,0 >600 300 +,+,+

123950 5-CH 3 6 200 60 0 500 150 +

144976 5-Cl 7 100 50 0 500 200 +9+

144975 5-Br 7 225 100 + 800 400 +(T) ,,O

145724 5-1 7 200 100 +,0 >750 600 +(T),0

94543 5-Br 8 230 50 0 >600 150 +

94532 5-Br 10 50 25 0

736

TABLE 33

Substituted 2-[(3-thiazolidinylalkyl)oxyquinolines

A k~ (01 )14iijA- • 0 (Ct 2)n-o

IN•RAPERITONEAL DATA ORAL DATA

ALD 5 0 Drug Dose ALDS 0 Drug DoseWE NO. A n mg/kg mg/kg Rating mg/kg mg/kg Rating

104705 4-013 2 250 50 0

106161 H 3 120 60 +,0 375 150 0

122958 4-OCH3 3 225 100 0 >900 500 0

136178 4-CF3 3 >360 40 0 >900 600 0

61134 4-CH3 3 320 180 +(T) >900 500 +

111487 4-CH3 ,6-Cl 3 350 70 +,0 >900 600 0

117930 4-CO3 ,8-Cl 3 >400 50 +,0 >900 500 +

146098 4-CH3 ,6-0C 3 3 200 100 0

123951 4,6-(C1 3 ) 2 3 500 50 0 >500 500

106163 4-CH3 4 260 110 0 600 300 0

108501 H 5 225 100 +,0 400 200 +,0

111488 4-Cl 5 350 150 0 >900 500 0

123948 4-0013 5 >450 50 0 - 200 0

132196 4-CF 3 5 200 50 0 800 400 +

43894 4-CH3 5 430 320 0 >600 300 0

"17883 4-CH3 ,6-C1 5 >375 300 +,0 >450 400 0

123952 4-CH3 ,8-Cl 5 180 60 0 >900 600 0

123949 4,6-(CH3 ) 2 5 500 6 0 >600 400 0

106158 4-CH3 6 200 100 0 850 450 0

737

TABLE 34

Substituted 2-[(3-thiazolidinylalkyl)thiopyridines

fr~~jS-(CH 2 ),j-1 7

INTRAPERITONEAL DATA ORAL DATA

ALD5 0 Drug Dose ALD5 0 Drug Dose

WR NO. A n rA_/k mg/kg Ratin& mg/k mg/kit Rating

132195 5-Cl 3 200 50 0 625 170 0

138768 3,5-Cl 2 3 225 100 0 950 500 0

157310 5-1 3 350 150 0 >600 300 0

159574 5-Cl 4 250 100 0 550 300 t(T),O

159618 3,5-C12 4 350 300 0 >650 300 0

159619 5-Br 4 275 100 0 650 300 +

162862 5-I 4 225 125 +,O 600 300 ±,0

126455 5-Cl 5 180 90 +,0 675 300 +,0

138417 3,5-C12 5 >300 100 +,0 1000 500 +

132192 5-Br 5 275 100 +,0 800 400 +,+

156717 3,5-Br 2 5 >503 200 0 >600 600 0

134787 5-I 5 175 50 +,o 700 300 +,+

132194 5-Cl 6 225 100 +,o 700 300 +,+,0

138769 3,5-C12 6 275 140 +,+ 1000 400 +,0

162863 5-Br 6 300 200 +,+ 500 400 +,+

152925 5-I 6 225 125 +,0 >438 250 +$+

166839 5-CH3 6 175 40 0 >300 300 +,+

158490 5-Cl 7 56 30 +,0 650 300 +(T),+(T),+,0

162818 3,5-C12 7 275 125 0 1>1050 800 0

738

TABLE 34

(continued)

INTRAPERITONEAL DATA ORAL DATA

ALD50 Drug Dose ALD5 0 Drug DoseWR NO. A n ma/kg ue/kg R mg/kg M/kS Rating

162864 5-Br 7 115 75 +,0 450 300 +,+

162865 5-I 7 125 100 +,0 300 200 +,+

160442 5-Cl 8 125 70 0 500 250 +(T),+,+90

162866 5-1 8 150 100 0 250 200 +,0

158498 5-Cl 10 135 90 O(T),0 >750 300 _(T),O

162857 3,5-Cl 2 10 525 250 0 >2000 1000 0

159621 5-Br 10 130 60 0 >600 400 0

739

TABLE 35

3-[(Alkylthio)alkylJthiazolidines

CH 3 (CH 2 )mS (CH 2 )n"-l

INTRAPERITONEAL DATA ORAL DATA

ALD5 0 Drug Dose ALD5 0 Drug DoseWR NO. m n mg/kv mg/kg Rating mi/kg mg/kg Rating

157843 5 2 250 125 +(T),+ >600 300 +(T),_

156715 6 2 250 100 +(T),O 550 250 +,0

156716 7 2 150 100 0 >600 400 +,0

156718 8 2 250 100 0 >350 300 0

154975 3 3 300 80 0 >600 300 0(T),0

154977 5 3 120 75 +,0 >300 200 +,0

157841 6 3 175 100 0 500 300 +30

136179 7 3 125 50 0 >600 400 +,+,0

157076 8 3 250 100 +,0 >600 600 +,+

166826 3 4 350 125 0 650 300 +,0

166830 4 4 175 67 +,0 600 200 +,0

166836 5 4 110 60 +,0 500 300 +(T),±

157073 6 4 175 80 +,+ 600 300 +(T),O

156714 2 5 300 75 0 >600 300 O(T),O

132727 3 5 160 60 +,0 900 250 0

157311 4 5 125 100 +(T),+,0 650 250 +,+,+

134783 5 5 75 30 +,0 500 250 +,+#+

158495 6 5 100 50 +,+ 500 150 +,0

99580 7 5 120 60 +,0 >525 400 +,0

99585 9 5 125 so 0 >900 300 0

740

TABLE 35

(continued)

INTRAPERITONEAL DATA ORAL DATA

"• N.ALD~ 0 Drug Dose ALD0 Drug Dose

___N.___ mg/kgl Rain m g Mg/kg Rating

154976 0 6 100 60 0 500 300 0

152922 1 6 300 100 0 >600 300 0

152924 2 6 160 75 0 >500 200 0

154978 3 6 >150 50 0 >300 300 +,0

157072 4 6 150 80 +,+ S00 200 +,+,0

154979 5 6 125 60 +,+ 175 90 +,0

157079 6 6 130 50 0 >1000 400 0

154980 7 6 >200 100 0(T),0 650 300 0

156720 8 6 150 80 0 >600 300 0

154976 0 6 100 60 0 500 300 0

157312 3 7 175 80 +,±,0 650 300 +(T. ,.

741

44 0

J in 0600

0 L0

0 0

Aj +1

on v

41A C31 0+10 +n m 00 +g

.- 0 0 Owl Q 0 0 0 '0 0 Ui 0

tO M At .4 "4 -T

N IqA :

co cN O 0n %JO o% cn G AP

P4 r t N .4 en - fn f4 en

742

.4na

0i C 0 0.- %- -%14 .

%04.

0 t 0 Ua 0 IJn 0 im WU 0 N ~ -N~ in NND N N C 4 ( 4 -

In 0 0 in 0 go ~ 0A 0 000

N a N C4 ( 4 C 4 C 4 C 4 C

N N N 0- a

Nn NN- t

-at 15 r'- -4 a- 'o-4@ ~eq %w-, Nc N 'mI I~ O@ N mN N

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c74

-~~~~ .. . .- ..~~ . ... .- - .

be ~ ~ C4 0n & 4 ý

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cn -4 C4 CON r

lz (4 m n M m m CI C n c

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C4Ln LO In %n mA m ~ (0-- -I - f-

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a 0%C4 C4 r- inN 61 n

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747

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7484

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753

H7--~- 7 -77 Y -- 7777

TABLE 40

Parent Acetamidine Derivatives

H2Nc (-NH) cH2SY

INTRAPERITONEAL DATA ORAL DATA

ALD50 Drug Dose ADS0 Drug DoseWR NO. Y mg/kg . mg/kg Rating mg/kg mg/kg Rat:ing

76842 H 52 24 +,+,0 150 80 +(T),+,+

166817 SCH2C(-NH)NH 2 60 25 +,+,0 125 50 +,+,_,o

1551 SO 3H 87 50 +,+,0 300 130 +,+

108250 Po 3H2 100 75 +(T),+ 135 75 +,+,0

754

&J +1+1S+ 00+1 +0

04 toa 4 f (nG

0n , %n c0oc N n

0h

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P4A

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oo ad

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tnzI r l o r oC ý 0 V OC4C 4 so C V

O755

0 0 0 0

000

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0 + 0

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N

N N� N

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756

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41 a1

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765

0 a

LM~ ~ 0 0cn ý O o o

4IS A A A A A A

0a C-

C) +1 0) +1

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.. a. ~ n-. g4

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C4 ,i4 C4 P N N

N "4-4 ~ D m r4P

t. -D %a % N No %0 N M

f-4 O 0% P4 %V '0 '0 " 0% at m en0 ON 0% 0 0% NO m0 0% 0% %a 0% 0%

r4 N4 -4 . r-I r-4 v-I r- V4 v-4

766

+1 + +

1644

in @i

&n~ 0 0 in inA - -4 ** V~4 V-4

414V 0ý

_n 0

(40 g. .n

r-4~ N --

41o (l n 4 4 4 T ~ X

*~~~ ~ 0% P ' s O~ % V~0 0% N- P

N% 0% 0% 0P4%."4 (4 4 "4 4 ~-40 .t-40

767

+1

41 + o

-A is 0 1i%. 0 0n 0 a~000 iI* 04n~ '

0

co0

0 0 0

41 0n co 0NP

0

Q 04 1-4rW4

4c

00

u *P

C4 N

0 r

ol 5- %0G -

r-4 -- OD .-4 %0.

76

+ +10 4+1a W1

0i 01 0

Q- 0I0 000

A4 A A

+ +a a 0ý47

L)+ + 0 + aý+ +U 0

o o- -7 0 - U)C

"4 £' w 0 0 0 0 %D 0 L 00

000c 0 0 0 00

00 Qs -~%0 0 (D ~oa O N 0% - . .

A A

NCAlo - U) 4

w -~ N

w In461., U) U Ur

-N N C4-048 fn - n -

Pi 0 0 0~

NC. Go t n 1 -4m fl (7 0 i

z %D % o% %D el C" enON 11 o w 0% ws ON

-I N .-4 ,4

769

TABLE 48

Compounds Effecting at least 50% Survival at a Dose of OneFourth of the Highest Dose Tested, either I.P. or P.O. andthe Table in which the Data Appear other than the Survey

WR NO. TABLE WR NO. TABLE

1964 46 138412 292529 Survey 151325 372578 37 151327 392823 27 158490 343050 14 168643 474546 22 176241 104788 22 176542 105035 25 179209 106402 25 183977 106403 25 183978 377467 25 187093 10

44923 39 187094 1054204 30 187144 4776842 46 190072 3776843 Survey 190222 3982422 29 193702 991635 25 194423 1094293 44 197487 4594542 32 199270 45

122960 30 199737 42122970 30 204172 44

770

TABLE 49

Compounds Effecting at Least 50% Survival at a Dose <15 mg/kg,Either I.P. or P.O., and the Table in which the Data Appear.

WR NO. TABLE WR NO. TABLE WR NO. TABLE

1607 11 16817 46 166832 451818 11 24245 44 166834 452245 12 32379 43 166843 452411 12 76842 40 169403 452691 25 92973 44 171079 432866 25 94140 44 181612 453050 14 94292 44 190222 393238 25 94293 44 193678 4:53302 25 109342 45 193681 453336 22 122960 30 193682 453337 14 138412 29 193687 443339 25 138415 20 196264 453340 14 142079 44 196265 453342 14 145837 44 197487 453358 12 146092 43 197490 453561 25 149750 44 197516 453566 25 150632 44 199270 453610 20 150633 44 199271 443824 25 150637 44 199737 423825 25 151331 45 199739 454104 25 156917 44 199740 454105 25 166717 44 199746 454538 20 166764 45 199747 454539 25 166817 40 201722 454544 20 166820 44 201724 254548 14 166823 41 201727 454769 22 166825 45 204157 454783 14 166827 44 204158 445035 25 166829 44 204159 445984 25 166831 44 204172 446403 257467 25

771

WALTER REED NUMBER INDEX

WR No. Molecular Formula WR No. Molecular Formula

1 C3 H3 N3 S3 83 C14H16N10S2

7 CHo23 NS 84 C10Ho1NS2

9 C5H9NOS 85 C10Q13NOS 2

11 C3H6N2S 86 CH2 S 3

12 C7 H1 5 NS 87 C5 H1 0 BrNS 2

13 C H9NS2 88 C3H803S3

17 C8H1 9NS 90 C6H 15NS

31 CjoHqN0 2 S 93 C2 0H4 4N2 S2

32 C4H9NS2 111 C H 21NOS

35 C7H7NS 112 C6Hi4N2S

36 C6H6N2S 118 C6 15NO9S6

37 C06N2S 119 C6N6S6

38 C6H6 N 2S 120 C4 H5 N3 0S 2

41 C8 H9 NS 121 C6 H9 N9 S 3

43 C4 H11 NS 122 C1 6 H3 4 N4 S2

44 C5H1 3N3S 123 C7H1 2N4 S2

48 C3 H7NS3 125 C3 H7 N05 S2

50 C7H8S2 141 C5HioS 2

70 C12H28N2 2 145 C2H5NOS

71 C4 H6 N2 S4 149 C10H2 3 NS

79 C1 6 H3 3 NOS 154 C7 H9 N5 S

80 CH CiNOS 155 C51 NOS

81 C4 H9 NOS 156 CH 4 02 S2

773

WR No. Molecular Formula WIR No. Molecular Formula

158 CIOH1 3NOS 2 195 C7H1 3NO3S

159 C8 H9 NOS 196 CI H 1203

160 C5H8 N202 S 197 C7 H1 ON20 4S

161 C3H8 N2OS 199 C7 H1 3NO6 S

162 C7H17NS 200 C7H1 3NO5 S

163 C6H1 5 NS 203 C6Hl3NS

166 C3H9 NS 205 C5H8 N2OS

169 C5H 3NS 206 C7H9NS

174 C3H8 S3 207 C7H9NS

176 C7 H1 6N2 S2 208 C8H1 1 N3S

177 C6 H14 N2S2 209 C8 HIIN3 S

178 C5H1 3NS 215 C4H 1N3S

179 C3H8N20 3S2 217 C9H13NS

180 C2H3N3 S2 218 C1 2H2 7NS

181 C8H8 N2 S 221 C6 H1 3NOS

182 C3H9N02 S2 222 C1 2H2 7NS

183 C9HI2 N20 2S 223 C6 HAMNS

186 C3H9 NS 224 C6H1 5 NS

187 C8H 7NO5S 225 C1 oH23NS

189 C7H1 3NO5 S 226 C1 0H23NS

190 C9H11NOS 227 C8 H1 7 NS

191 C5H12N 2 S2 228 C1 2 H2 7NS

192 C7Hl3NO4 S 229 C6 H1 5NS

193 C6H1 1 N04 S 230 COH 23NS

194 C HN15N4S 231 CH 11NS

774

WR No. Molecular Formula WR No. Molecular Formula

232 C8H 19NS 337 C4H7NS2

233 C7Hi6 N2S 338 C4H 8N2S

234 C8H19NS 339 C4 H NS

237 C3H4 N2OS2 340 C7H1204S

245 C6H1 1 NS 341 C7H1 4 0 5S

246 C8 H1 6N20 2 S2 342 C H 20N202 S2

247 C12 H2 0 N206S 2 346 C3H8 N2OS

248 C18 Hj8 N2 S2 347 C2 H 7NS

249 C9H2 1NS 348 C3 H 7NO 2S

256 C1 0 H2 3 NS 351 Co H17N306S

257 C2 1H4 5NS 352 C4H 2N 2S2

258 C3 H9N03 S2 357 C7H1 7NS

259 C5 H1 3NO3 S2 358 C9H2 1 NS

260 c9H21N 7 S3 359 C2 2 H22 N4 02 S2

261 C3H8 N2OS 361 C2H7N03S2

298 C3H9 N3 S 362 C4 HINO3 S2

305 C3H5 NS2 363 C3H9 NO3S2

312 C5 H1 1 NS2 364 C4 H1 1 NS

315 C3 H 9NS 375 C2 0H2 4N2 02 S2

316 C1 2 H1 7 NS 377 C5 H1 1 NO2 S

318 C10H15NS 382 C8 H NS

319 C6 H oN202S 383 C6 H1 004 S2

322 C9H1 7 N07S 384 C2H6N20s

323 C7H7NS2 385 C4H8 0 2S

334 C5 H1 oN2 S 386 C3 H N 2S2

775

WR No. Molecular Formula WR No. Molecular Formula

387 C3 H4 S 3 563 C3H5 N03 S2

388 C5 HIINS 571 C8 H1 4 N20S

389 C6 HI 1 NS 572 C5 H8 N4 S2

390 C6 H1 3 NS2 591 C6 H4 N2 S

391 C1 1H10N2S 592 C6 l 1 2 N2 s 4

392 C6 H8 N2 S 594 C6HJ2N2S6

401 C8 H1 4 N4 S2 598 C4 H9 NOS 2

415 C5 H9 NOS 2 599 C1 2 H1 6 N6 S 2

419 C4 H9 NO2 s 600 C5 H1 3 N3 S 2

424 C6 H1 3 N02 S 601 C1 2 H2 0 N2 0 2 S4

464 C4 H1 0 02 S 2 608 C5H5NS

454 C7 H8 02 S 609 C1 6 H3 2 N2 0 1 2 S2

528 C9 H8 02 S 610 C6 H1 5 N3 S

529 C4 H9 N04 s 611 C4 H1 1 N3S

530 C3 H 6N 2S 612 C6 H1 5 N3 S

531 C8 H1 4 N4 S2 613 C6 H1 0 N2 02 S

532 C6 H1 2 N2 S 614 C1 1 H9 N3 0 2 S

537 C8 H1 7 N05s 615 C9H 3NS

538 C6 H1 2 N4 S2 618 C7 H 4N 2S

539 C3 H8 N2 S 619 C 16H 23NO 9S

540 C2 H6 N4 S2 620 C 18H 18N4S4544 C4H8N202S2 621 C5H 13NS

550 C4H12N2Se2 622 C4 H9 NOS

551 C1 1 H2 1 NO5 S 623 C5 H1 3 N3 S

552 C7HI NOS 624 CH 15NS

776

WR No. Molecular Formula WR No. Molecular Formula

625 C7 Hi 5 NS 655 C4 H 7N 3S

626 C9 H1 6 N4 S2 656 C4 H9 N3 OS

628 C1 4 H1 4 02 S2 657 C9 H1 8 N6 0 2 S2

629 C3HoN3 0S 658 C8 H1 7 N3 0S

630 C9 H9 NS2 659 ClOH1 3 N3 OS

631 Cl0Hl5N03S2 660 C5 H1 1 N3 0S

632 C9 H2 0N2 S 661 C4 H8 N20 2 S

633 C8H 1NS 663 C4H1 0 N2S

634 CI 3 H2 0 N2 S 664 C4 H1 oN2 S

635 C1 2 H19 NS 665 C4 HsN2 S

636 C6 113NS 666 C2 H 6N 2S

637 C4H 1O3PS 667 CH 17NO4S

638 C2H 8NO 3PS 668 .C6H 15NOS

639 C 6H 16NO 3PS 669 C2 H3 N3 S

641 C6H 13N3 670 C4 H2N2 04 S

642 C9 H1 0 N2 0S 672 C3H 7NO2 S

643 C6 H1 3 N3 S 673 C1 0 H1 3 NO2 S

644 C1 3 H1 3N3 0 2 S 674 C7 H1 7 N5 S2

645 C1 1 H1 1 N3 02 S 675 C9 HloN2 S

646 C7 H1 5 N3 S2 679 C3 H9 NS

647 C5 Hl2 N2 0S 2 680 C4 HOUNS

648 c5H13N3 S 682 C1 4 H1 5 N30 2 S

649 C1 0 H2 0 N6 S 2 683 C1 2 H1 3 N3 0 2 S

650 C1 0 H1 8 N4 S4 684 C8 H1 5 NOS 3

651 C5 HI 3 NS 685 C4 H6 S3

777

WR No. Molecular Formula WR No. Molecular Formula

686 CI6H28N 2 02 S6 734 C8H1 7NS

689 C6 H1 5 N03 S2 741 C7H1 5NS

691 C5H1 3NS 746 C6 H N 3S

692 C16H32N 2 S2 747 C6H14 04 S4

693 C 18H 25NO 1S 748 C8H oN2S

694 C5H oN20S 749 CH 12N2S

695 Co H 1NO3S 750 C 10H9NS

696 C1 1 H1 3 NO3S 751 C 10H 20N 2S6

697 C6H15NS2 753 C 14H 24N202S6

698 C4 H NOS 754 C1 6H1 8 N4 S2

699 C6 H1 5 NOS 755 C1 6 H2 2 N4 S2

700 C8H 9N3S 757 C4H MN3S

701 CH4N2S2 760 C6 H1 6 N2S

702 C2 0H20 N2 04 S2 761 C1 6 H1 9 NO4 S2

703 C2 0H2 0 N2 06 S2 762 C16 H1 9 N04 S2

704 C14 H2 1 NO8 S 763 C6 H1 3 NS

707 C6 H N 3S 764 C1 2H2 2N2S3

709 C3H2NO02S 766 C2HsNOS

710 C3H3N30 2 S 767 C5H1 2N2S

727 C5 H1 3NOS 769 C8 H1 1 NO3S2

728 C4H12N202S2 770 C1 2 H1 7NS

729 C6H1 5 N5 S2 774 C6 H9N3S

730 C6H8 N2 OS 776 C H 0N 2S3

731 C3H3N3 OS 777 C1 2 H1 5 NOS

732 C9 H8 N4 03 S2 778 C8 H2 0 N2 S

778

WR NO. Molecular Formula WR NO. Molecular Formula

779 C8 H1 7 NS 810 C3 H 5N302S

780 C4 HIINS 811 C1 8 H2 3 NS2

781 C8 H1 9 NS 812 C8 H NO4 S

782 C1 oH2 1 NOS 813 C6 H1 3 NS

783 C4H9N3S3 814 C4 H1NS

784 C7H9N3 S 815 C12Ho10CN03S

785 CloH15NS 816 C1 2H1 1 NO3 S

786 CIOH1 4 CINS 817 C13 H1 3NO3S

787 C16 H20 N2 S 821 C11 H1 5NOS 2

788 C7H1 2N2S 822 C1 6H1 4 06 S2

789 C3H7NOS 823 CIOH2 0N2 02 S4

790 C11H1 4N2S3 826 C7H 2N 2S

791 C2 0H24 N2 S4 827 C5H13NS

792 C1 0H1 5NS2 828 C1 0H1 5 NS

794 C6H7NS 829 C6H15 NO2S

795 C7H9N3S 830 C8Hi 7NOS

796 C8 H1 7N3S 831 C9 H2 1N02 S

797 C9 H 11NS2 834 CH 13NS

799 C6 H 10N 2S 835 C1 2H 1 3NS

800 C8HI6N204 S2 836 C1 3H1IN 3S

802 C6H1 5N03S2 837 C1 3 H1 1 N3S

806 C H 3NSe 839 CsH1oN2S

807 C1 oHI 3 NO2 Se 840 C7 H 2 N2 S

808 C1 2H1 5NO3 Se 841 C7H 1 4N2S

809 C1 2H1 6N604 S2 842 C9H20N2 S

779

WR NO. Molecular Formula WR NO. Molecular Formula

843 C6 H1 5 NOS 880 C5 H1 3 NOS

847 C8 H 9NS 881 ClIHI 7 NOS

848 C3 H8 N2 S2 882 C9 H1 7 NOS

849 C5 H1 oN2 S2 883 C H 17NS

850 C1 4 H2 6 N4 0 2S 2 884 C4 H1 2 N2S

853 C4 H5 N30 2 S 885 C6 H1 5 NOS

854 C3H4N4OS 886 C6H1 5 NS

855 C1 8 H1 4 N4 S2 887 C9 H1 9 NS

856 C9H1 9NS 888 C5 H1 3 NOS

857 C8 H2 0 N2 S 889 C4 H1lNS

858 CH 14N2S 892 C8HI 7NO3S2

860 C4 H 4N 20 2S 894 C1OH1 9NOS

861 C1 6 H1 0 N2 02 S 895 C6 1.1 5 N02 S

862 C4 H5 N5 OS2 896 C1 1 H1 8 N20 3 s 2

864 C4H8N204S2 897 C7H 12OS

865 C3 H7 NOS 898 C9 H1 4 0 3 S

866 C6 H1 3 NO4 S 900 ClOH1 2 0 2 S

870 C9 H1 2 02 S 901 C4 H 6OS

871 CIlH9 CIN2 S 910 C8 Hs 5 N5 S2

874 C6 Hl5 NO3 s 2 912 C1 0 H8 S3

875 C5 H9 N3OS2 914 CsH1 9 NOS

876 C9 H1 9 NS2 915 C7 HI8N2S

877 C7 H1 5 NO4 S 916 C H 13NOS

878 C8H 19NOS 917 C 921NS3

879 C12 H NOS 921 C7H 17NO2

780

WR NO. Molecular Formula WR NO. Molecular Formula

922 C9 H2 0N2 OS 985 C4 H9 NO2S

923 C10H12N203S2 986 C4 H6 N2 04 S

924 C6 H1 5 NS2 987 C2 H 4N 20 S

927 C9H13 NS2 988 C4H4N2OS

928 CTH9NS2 989 C1 1 H 14 N2S

929 CHoNS 990 C6H NS510N2S 613

931 CTH NS 991 C H NS17 11 2 16 13

932 C1 0 H2 0 N2 S2 993 C4 H NOS

934 C9 H1 0 N2 S2 994 C5 H NS

935 C1 2 H1 8 N2S 2 996 C7 H NO3 S2

936 C7H1 6 N2 S2 997 C8H INS

937 C8 H1 3 NS2 998 C8 HIANOS

940 C6 H0 0N 40 2 999 CSl 1 NS

941 CsH1 3N3 S2 1000 C8 H1 1 NOS

956 C8H1 7,10S 1001 C7 H NOS

957 CsHI1N 2 S 1002 C1H 2N 2S2

9511 C9 H2 1N2 S 1032 C9H1 9NO5S

959 C8 H1 9 NO3 S2 1GJ3 C5 H1 3 NO3 S2

960 C8 H1 9 NO3 S2 1036 C4 Hl1 N03 S2

962 C3 H7 NOS 1039 C9 H1 7 NO5 S2

977 C9 H1 7 NO7 S 1040 C7 H1 8 N2 S

978 C8 H1 5 NO6S 1042 C3 H8 N2 OS

982 C5 H1 3 NO3 S2 1043 C6 H1 5 NOS

983 C6 H1 3 NO4 S2 1044 C4 H7 NS2

984 C4 H1 1 NS 1045 C9 H2 2 N2 S

781

WR NO. Molecular Formula WR NO. Molecular Formula

1046 C8H11NS 1075 C8 H1 4 0 4 S

1047 C9H1 3N03S2 1076 C5 HIINO2S

1048 C9 H1 3 NS 1077 C8 H1 4 0 2 S

1050 C8 H1 1 NO3 S2 1079 C7 H1 8 N20S

1051 C1 1 H1 2 N20S 1080 C5 H4 N4 S2

1052 C4 H7 NS2 1081 C6 H1 5 NO3S 2

1053 C9 H1 9 NS 1082 C7 H 15NO3 S2

1054 C6 H1 5 NS 1083 C H 2N 2S

1055 C9 H6 S3 1084 C6 H1 3 NO4 S2

1056 C6 H1 5 NOS 1085 C6 H1 3 NO3 S 2

1057 C1 1 H2 6 N2 S 1086 C5 H1 3 N03 S2

1058 C1 1 H2 1 NOS 1087 C3 H9 N3 03 S 2

1059 C7H1 0 N2 0 2 S 1088 C4 H6 N2 S

1060 C7HIoN2 OS 1089 C6 H1 6 N6 S 2

1062 CllH2 1 N03 S 1090 C5 H1 3 N03 S 2

1063 C9 H 22N 2S 1091 C2 H6 N2 S

1064 C7H 7NOS 1093 C7H 7NO3S2

1065 CH S14N2S 1094 CH 13NOS32

1066 C6 H1 6 N2 S 1095 C4 H1 1 N03 S2

1067 C6 H1 5 NOS 1096 C7 H1 7 NOS

loUt C6 HIINS 1097 C1 6 H2 7 N3 03 S2

1069 C6 H1 1 NS 1098 C8 H1 7 NO3S 2

1070 C5 H1 1 N3 S 2 1099 C5 H1 3 N03 S2

1072 C H 19NS 1100 C7H 17N052

1074 C1 0 H1 6 055 1101 C H 17NO3 S2

782

WR No. Molecular Formula WR No. Molecular Formula

1103 C8H1 9NOS 1129 C 44H 40N6 S2

1104 C6 HI 5 NOS 1130 C7 HisNS

1105 C4 H1 1 NO6 S4 1131 Cl 4H21 NO8S

1106 C8 Hi1N 3 03 S 1140 C H 2N2OS

1108 C5 H6 N2 0 2 S2 1143 C8 H1 0 N2 OS

1109 C6H9NS2 1144 C7H1 7 NO3S 2

1110 C7H1 5 NO3S2 1145 24H1 1N30 3 S2

1111 C8 H1 4 N2 S 1146 C4 H6 N20 3 S3

1112 C9H 3NO3S2 1147 C6H 2N4S2

1113 CH 17NOS 1148 C 6K 12N2 S

1114 C1 4 H2 8 N2 S2 1149 c12H22N203S2

1115 C6 H1 4 N4 04 S2 1150 C6 H1NO3 ,

1116 C6 Hl 1 NS 1151 C6 H1 6 N2 0 2 S2

1117 C 10H 19NS 1152 C3H9 NO3 S

1118 C5 H9 N05 S2 1153 C6 H1 2 N2 0S

1119 C5H 13OS 1154 CH 10N202S

1120 C5 H1 3 NO2 S 1155 C7 H13 NO3 S

1121 C8 H1 7 NOS 1156 c 1 1 H9 N3 S

1122 C1 H1 9 NO2 S 1157 C6 H1 2 N2 0 2 S

1123 C9 H2 2 N2 OS 1158 C8 H14 N2 S

J.124 C1 0 H2 3 NO2 S 1163 C2 H4 N4 0 2 S

1125 C7 H1 4 N2 OS 1164 C4 118 N2 02 S

1126 C7 H1 4 N2 S 1165 C5 H1 1 N3 S

1127 C1 3 H1 7 N3 0 3 S 1166 C6 H1 2 N2 02 S2

1128 C8 H1 6 N2 S2 1167 C1 6 H1 6 N20S

783

WR No. Molecular Formula WR No. Molecular Formula

1168 C8 H2 4 C1 2 N4 Ni 3 S4 1245 C1 0 Hi 5 NOS

1169 C8 H2 4 Br 2 N4 Ni 3 S4 1247 C5 H1 3 NO6 S4

1170 C6 H1 8 CoN 3 S3 1248 C7 H1 4 N4 S2

1172 C9 H1 3 N03 S2 1249 C5 H1 3 N3 S

1173 C8 H1 1 N03 S2 1250 C1 0 H2 3 NO3 S2

1174 C1 1 H 2 N206S 4 1251 C4 H1 1 N3 S

1175 C1 6 H2 2 N4 S 1252 C1 6 H2 7 NO3 S2

1176 C1 2 HI9 NO3 S2 1253 C1 3 H1 9 NO 3 S2

1177 C1 2 H1 9 NS 1254 C1 4 H1 7 NO3 $2

1178 C1 6 H2 7 NS 1255 C1 4 H2 1 NO3 S 2

1179 CI 4 H2 1 NS 1256 C1 0 H1 5 NO3 S2

1182 C1 2H19NS 1257 C1 2 HI 9 NO3 S2

1183 C1 5 HI7 NS 1258 C11 H17NO S2

1184 CloH1 5NS 1259 C5 H5 NOS

1185 C1 3 H1 9 NS 1260 C6 H7 N3 OS

1186 C5 H1 3 N3 03 S2 1261 C9 H1 9 NO5 S

1187 C4 H5 NO2 S 1262 C7 Hl 3 NOS

1188 C7 H1 5 NOS 1263 C7 H1 3 NOS

1189 C1 9 H3 7 N3 0 2 S 1264 CloH1 8N2 0 2 S

1190 CloH2 3 NOS 1265 C5 Hl 3 NS2

I1CI C6 H1 5 NOS 1279 C8 H2 4 Cl 2 CuN4 NI 2 S 4

1192 C2 0 H2 4 N2 0 3 S 1280 C8 H 24 Cd2C4N4Ni2S4

1224 CH 6 N4 S 1282 C8 H2 4 C1 2 Co3 N4 S4

123' C9 0 N2 0 2 S 1283 C8 H2 4 C1CuN4 NI 2S 4

.-44 C7 HI1 5 NOS 1284 C1 2 H3 6 Br 2 Co2 N6 NiS 6

784

WR No. Molecular Formula WR No. Molecular Formula

1285 C1 2H36 Br 3 Co3N6S6 1453 C6 H1 5N30 3S2

1290 C4H1 1N30 3 S2 1455 C5 H9 NS

1291 C5 H 3 N3 03 S2 1457 C1 7 H1 7 N30S

1292 C6 H N 20 2S 1458 C6 H1 3N303 S2

1317 C5 H N 20 2S 1459 C6 H9NOS 2

1366 C1 8H20 N20 3S 1460 C6H1 5 N3 S

1424 CloH21NS 1461 C6H 1NS

1426 C5H 3NS 1462 C8H 9NS

1427 C H16N604S2 1463 CloH24 N202 S2

1428 C4H9N3 02S 1464 C7H1 6N2 S4

1430 C8 H2 4 C12 N4 S2 1465 C1 2 H20 N2 04 S2

1431 C3H7NOS 1466 CH S13N3

1432 C3H6 OS2 1468 C7 H1 3N3OS

1434 C5HIIN03S2 1469 C6H 17BrN4S

1435 C6 H1 5 NOS 2 1470 C H 15NO3 S2

1436 C8 H 9NOS 2 1471 C8 H1 9N03S2

1438 C7 H 25NO9S2 1472 C1IH 2 5N03 S2

1440 C H NOS 1473 CI3H29NO3S2

1443 C8 H NOS 1476 C3 H8 N2 S2

1445 C6H 1NOS 1477 C5HII N3S3

14C913N03S2 1479 C5II NS$1446 C9H 13NO 3S 249c5 H11N3 S3

1447 C6H1 5 NO2 S2 1480 Cd18N2 NO2 S

1450 C4 H5 NOS 2 1481 C7 H NO2 S1451 C4H11N303S2 1432 C 3H24N202S2

1452 C H 3N 3S 1483 C8 H2 0 N20 4S2

785

WR No. Molecular Formula WR No. Molecular Formula

1484 C3119 NO3 S2 1522 C9 H2 1NS

1485 C5H14 N4 S2 1526 C4 H9NO3 S2

1486 C6 H7NOS 1527 C8 Hl6 N2 04 S2

1487 C6H7NOS 1528 C1 oH1 1 N30 3S2

1488 C4H1 1 NO3S2 1529 C H oN 2S

1489 C5H1 2 N2S 1530 C9 HI2N20 3S2

1490 C4 H1 2 NO3PS 1531 C4 Hl0 N203 S2

1491 C7HgN4 S2 1532 C3H8 N2OS

1492 C9 H14 N2 03S2 1533 C7 H 3NO2 S2

1493 C1 2H1 4 N20 3S2 1534 C1IH1 3 NO3S2

1494 C3H9N3 S 1535 C3H7NOS

1495 C6H1 5 NS 1536 C4 H NOS

1496 C6H15 NS 1537 CH011 NOS

1500 C9 H1 9 N02 S4 1538 C7H11 N02S

1504 C9H15NS2 1539 C4 H 9N 3OS

1503 C1 3 H2 5NS2 1540 C9 HI7N04 S

1506 C1 0H1 3NOS 1546 C4 H6N202 S2

1507 C H 23NS 1547 C H 25NS

1512 C6H15 NS 1548 C9H21 NS

1513 C9H1 7NS 1549 C1 3H2 9 NS

1514 C11 H2 5NS 1550 C3H9 N3OS

1518 C1 2H2 7NS 1551 C2H6 N20 3S2

1519 C7H1 7 NS 1552 C3H8 N20 3S2

1520 CIIH2 5NOS 1553 C4 H11 NS

1521 C1 2H2 7NS 1554 C H 3NS

786

WR No. Molecular Formula WR No. Molecular Formula

1555 C6 H8 N2 OS 1608 C4 H1 1 N3 0 3 S2

1556 CI 2 HI 2 N2 S 1609 C5 HIl1NOS

1557 C H oN2 OS 1610 C8 H1 6 N2 0 2 S2

1558 C1 1 H1 1 N02 S2 1611 C8 H1 6 N2 04 S2

1562 C8 H2 0 N2 S 1612 C6 H1 3 N02 S

1563 C4 H1 oN4 02 S 1613 C6 H1 0 0 2 S2

1564 C6 H1 2 N2 0 2 S2 1614 C5 H1 3 NS2

1565 C1 4 H3 1 NS 1615 C1 8 H3 9 NS

1566 C1 4H 3 1 NS2 1616 C6H 15NO3S

1567 C9 H 15NO4 S 1617 C8 H1 8 N2 OS

1568 C6 H 15NS 1618 Co1 0 H2 3 N03 S2

1569 C7 H1 7 NS 1620 C7 HsNO4 S

1570 C4 HllNO3S 2 1621 C4 H1 1 NS2

1574 C3 H9 N3 S 1622 C5 H1 3 N3 03 S 2

1575 C1 5 H2 3N3 08 S 1623 C3 H9 NO4 S2

1576 C7 H1 2 N2 0 2 S 1661 C6 H1 5 N035 2

1577 C8 H1 2 N2 OS 1662 C6 H 15NO 3S2

1599 C7 H1 0 N2 0 2 s 1663 C6 H1 5 NO3 S 2

1600 C9 H1 3 N30S 1670 C1 1 H1 3 NO3 S2

1601 C1 0 H1 5 N30S 1679 CH 12N20 2S

1602 Cs5 H4 N4 S2 1680 C1 0 H2 2 N2 S

1604 C H 25N 3S 1681 CloH2 3 NS

1605 CllH2 5 N3S 1682 C9 H2 3 N3 S

1606 C1OH23NO3S2 1683 C5H1 3NS

1607 CI2 H2 7 NO3 S2 1684 C5 HIINOS

787

WR No. Molecular Formula WR No. Molecular Formula

1685 C5H9 NO2 S2 1723 C4 H1 1 NO4 S

1686 C7 H1 3NO2 S2 1724 C4 H1 0N4S

1687 C1 0 H2 2 N20 3 S2 1725 C6H1 3 N03 S2

1692 C1 0 H2 4N2 S 1726 C5 Hl3 NS

1693 C5 H11NOS 2 1727 C6 HI6 N2S

1694 C1 9H2 3N5 011 S 1728 C6 H16 N2S2

1695 C4 H1lNS2 1729 C7H1 8 N2S

1696 C9 H2 1NS 1730 C9H22 N2S

1697 C6H1 4 N20 3S2 1731 CIIH2 6N2 S

1698 C6H14 NPS 2 1732 C1 2H28 N2 S

1699 C4 H 10NOPS 2 1733 C9H19NS

1700 C8 H2 2N3PS 3 1734 C8 H 7NO 3S2

1701 C4H1 1N3 Se 1744 C7 H1 5 N3 S

1702 C5H 3N3Se 1745 C6H3 N3S

1703 C4 HA1 N3 Se 1746 C6 HAC1N 30 3S2

1704 C3H9 N3Se 1747 CloHI 1 N30 3S2

1710 C1 8H3 9NS 1748 C6H8N2 S

1711 C2 0H4 3NS 1749 C1 2 H2 2 N2 02S

1714 C1IH 2 1NO5S 1750 C6 H1 4 N20 3S2

1715 C7 H1 1 NOS 2 1751 C6H1 6N2 OS

1716 C8 H1 5 NO2 S2 1752 C8 H1 6N20 2 S2

1717 C8 H1 3NOS 2 1754 C1 7H2 7NOS

1718 C1 0H1 9NO2 S2 1755 C1 3H3 oN2 S

1719 C1 oH1 7NOS 2 1756 C9 H 12N 20 3S2

1722 CI2 HI6 N2OS 1.757 C3H8 N20 3 S2

788

WR No. Molecular Formula WR No. Molecular Formula

1758 C4 H1 0 N20 3 S2 1807 C8H 1 2N20 3 S2

1759 C5H1 1NOS 1808 C6 H1 3 NOS

1761 C2H6N4 S2 1809 C5 H9 NS2

1762 C6 H7 N3S2 1810 C5 H NO 3S3

1763 C7H1 5N3 S3 1811 C5H1 2N2 03 S2

1764 C1 6H2 9N3 S3 1812 C8H10N4S

1765 C9H1 2N2S2 1814 C H 24N 3PS3

1766 CIOH14 N4S2 1815 C4H10 NPS 2

1777 C1 8 H32 N6 02 S2 1816 C6 H 8N 3PS3

1780 C6H iNOS 1817 C2 H 3N3PS3

1781 C10H23NOS 1818 C11H 25NOS32

1782 C7 H 15NO 2S 1819 C6H1 5NS

1783 C51114 N2 OS 1821 C8 H2 1 N3S

1784 C8 H1 5 N02 S 1823 CqH1 9 N05 S

1785 C9H 8N2S 1824 CI H 6N2S2

1787 C1oH24 NOS 1826 C5H 1NS

1788 C6H1 5NO2 S 1827 C9H1 5NO2S

1789 CIOH21 NOS 1828 C1 2H1 7NS

1791 C7HI 7NOS 1829 C7H1 0N2 S

1792 C10H15NS 1830 C8H12 N2S

1800 C6 H N 30 3S 1831 C7 H8N2OS

1803 C6 H N03S2 1832 C8H10 N2OS

1804 C1 2 H1 9NS 1833 C1 4 H1 4 N4 02 S2

1805 C1 2H2 1 N3 S 1834 C7 H 0oN2OS

1806 C8H20N10S2 1835 C1 1H2 5N3 S

789

WR No. Molecular Formula WR No. Molecular Formula

1836 C1 8 H3 0 N4 S2 1888 C5 H9 N02 S 2

1837 C 12H 21NOS 1889 C5 H7 NOS 2

1838 C7 H1 5 NOS 1890 C8 H1 5 N03 S

1839 C5 H8 C12 N2 S 1891 C8H1 1NS

1867 C1 0 111 4 N2 03 S2 1892 C1 2 H2 8 N2 03 S

1868 c4H1oN203S2 1893 C 14H32N2S

1869 c13 H20N 2 03 S2 1894 C1 2 H2 8 N2 S2

1870 C4 H1 2 N4 S 1895 C1 2 H2 7 NOS

1871 CIIHI 5 NO3S 2 1896 C2 0 H1 6 N4 0 4S

1872 C10H17N3S3 1897 C H 13NO4S2

1873 C1 0H2 1N3 S3 1898 C14 H31 NOS

1874 C1 6 H1 7 N3 0 2 S 1900 C1 3 H2 1 N3 0 7S

1875 C1 0 H2 0 N2PtS4 1901 C7 H1 8 N2 OS2

1876 C1 0 H2 4 N2 S4 1902 C9 H1 2 N20S

1877 C1 oH2 4 N2 S2 1903 C5 H1 3 NO3 S2

1878 C2H7NO3 SSe 1904 C5H1 3N03 S2

1879 CloH2 0 N2 S4 Zn2 1905 C1 3 H1 7 N3 03 S2

1880 C1 6 H3 6 C1 2 N4 Pd 3 S4 1910 C1 7 H3 6 02 S2

1881 ClOH2 2N2S4 Zn 1911 C1 4H3 002S2

1882 C1oH2 2N2 PdS4 1912 C1 5H3 202S2

1883 C1 2H25 N3 S3 1913 C1 2H2 4 04 S2

1884 C2 H 25N302S 1914 C 21H 32N2S

1885 C1 2 H2 1 N3 06 S 1915 C2 0 H3 0 S

1886 C9 H1 1 NO2 S2 1916 C6 H13 NOS

1887 C6 HoN220 2 1917 C6 H1 4 02 S2

790

WR No. Molecular Formula WR No. Molecular Formula

1923 C7H6N2S2 1973 CIOH26N3PS 3

1937 C5H1 1NS2 1974 C4 H 7NO3S2

1938 C6 Hl2N202 S2 1986 C 3H 9NO4S2

1939 C4H1 0N20S 1987 C7H1 5NS

1940 C12H24N 2 06 S4 1988 C4 H11 N30S

1941 C1 4H3 1 NS 1989 C4 H1 oN2 S

1942 C6 H15 NS 1990 C5 R.'N 2 S

1956 C18 H2 2N4028 2 1;1 C9H 3NOS42

1957 C7H1 4 N203S ,3 1992 C1 1R1 7N02S

1958 C4H11 N30 3S2 1993 C1 2 H1 9NOS

1959 C10 H2020 N202 S4 1994 C16a19Ns

1960 C5HR11NS2 1995 C12a19 NO4S2

1961 C5HI14 NO3 PS 1996 C4HelNOS

1962 C41Q0.S . 1997 C6 H1 4N2OS

1963 CII.' 1.998 C1 4H2 6 N4 06 S2

1964 C "tji'.• 1999 C6H1 4 2 0S

1965 C1 4H3 1 NO3 S2 2000 C15 H2 9 N3S

1966 C2 2H2 2 NS 2002 C8HI7 NS

1967 CSH2 0N2 02 S2 2003 C7H1 7N02 S

1968 C1 1H1 3NU s2 2004 C7H1 7NS

1969 C6 R1 3NO3 S 2005 C1 2H2 4 N20 6S

1970 C8H1 6N2 02 S2 2006 CI12H2 4N2068

1971 C6Hl3N20PS2 2007 C1 3H2 9NO3S2

1972 CaH20N3Ops3 2008 C5 H1 3NO3S2

791

WP. No. Molecular Formula WR No. Molecular Formula

2009 C19 H2 7N30 10 S 2039 C7H1 6 N2 OS

2012 C H 24N204S 2043 C 10H NO7S

2013 C8H1 3NOS 2 2044 C10 H19 NO7S

2014 -s8H,3NOS 2045 C1 0oH 19 NO7S

2015 C1 4H22 N20 2S 2046 C1 7 H3 7NOS

2017 C3H5 NOS 2047 C19 H4 1NS

2018 C7H1 3N02 S 2048 C4 H 9NS3

2019 C4H9 N05 S3 2049 C7H1 4N20 3S2

2020 CHI oN202S2 2050 CHI2 N203S2

2021 C5H1 3N5 S 2051 C6H11 N02 S3

2022 C4H1 1N3S 2052 C6Hl1N3S

2024 C7H1 5NOS 2058 C H 13NS

2025 C7H1 5NOS 2059 C1 5H33NS

2026 C1 2H2 7NS 2060 C1 4H30N2 03 S2

2027 C4H1 0N20S 2061 C5i12N203S2

2028 C3R8N20S 2062 C H 9NO 3S

2031 C3H402S 2063 C6H 1NO3S

2032 C4H6 03 S 2064 C7H13NO3S

2033 C5H1 0 03 S 2065 C7 H1 1 N02 S

2034 C6 H12 04 S 2066 C1 oH1 9 N03S

2035 C5H1 0 03 S 2067 C1 0 H1 7N04 S

2036 C12 H 13NS 2068 C10 H1 7N02 S

2037 C10 H2 0 N2S2 2069 C11 H1 3N04 S

2038 C8 H16 N2 0 2S 2070 C8H1 4N2 S

792

WR No. Molecular Formula WR No. Molecular Formula

2072 C5H8N2 02S2 2096 C7H1 6N203S2

2073 C11 H23NOS 2097 C8 H1 6N12 03 S

2074 f1OH18N406S2 2098 3 H 22NO2PS2

2075 C14 H30N40 2S2 2099 C1 0H2 5 NO4P2S32076 cSH oN203S 2100 C8 H2 1N202PS 2

2077 C1 1H2 5NO3S2 2101 C9H 2 2N3PS 3

2078 C9H2 1N03 S2 2102 C6 H1 4NOPS 2

2079 c10H23 NO3S2 2103 Co1 0 N2 0 2S2

2080 C1 4H3 1 NO3S2 2104 C IH22N20 2S2

2081 C IHON302S 2105 C 11H 21NO2S

2082 C3H9 NS2 2106 C3H8N2G

2083 C4H1 1N3 S 2107 C6 H1 4N4 S2

2084 C1 7H3 7NS 2108 C H 13NO3 S2

2085 C5H1 3N03S 2 2109 C15 H3 3NO3S2

2086 C6H1 3NS 2110 C 13H25NO2S

2087 CsH1 5NO4 S 2111 C1 3H2 9NO3S2

2088 C8H1 7NS 2112 C5 H1 3NOS

2089 C4HsAgNOS 2113 C3 H 9NS

2090 c11H14N202S2 2122 C4 H1 5NO3S2

2091 C7H 7NS 2123 C8H 1NS

2092 C8H1 3NO2 S 2127 C5H11 NS

2093 C6H13NOsS2 2128 C H 21NS

2094 C8H20N20 4 S4 2129 C5 H F 3NOS

2095 C1 3H27 NO2 S 2130 C7 H NO3 S

793

WR No. Molecular Formula WR No. Molecular Formula

2131 C8H1 9NS 2178 C7H 1 7N03S2

2132 C9H2 1NS 2179 C5H1 3N3s

2133 C3H7NS 2 2180 C3 H8N2 04 S2

2137 C8H1 9 NO3S2 2181 C1 3H2 2N20 6 S2

2138 C5l 1NC2S 2182 c6H13N3S3

2139 CH15 N02S3 2183 C6H16N60 2S2

2140 C 66H13N03S 2184 c8H20N2S 4

2141 C6H 3 N03 S 2185 CH 1 4N20 30S

2142 C1 0H14 N203S2 2186 C8H1 0N2 0 3r12

2143 C5 H1 2N20 3S2 2187 C1 0H1 4N203 S2

2144 CgH 3N04 S2 2188 C 3H2 6NO 2 S2

2145 C3H9NO4S2 2189 C6 H16 N2 S,

2146 C H 15NO4S2 2190 C020NS2

2147 C7H1 1N02S2 2191 C14 H3 2N6S2

2148 C7H1 3N03 S2 2192 H24N202S2

2149 C7H1 3N04 S 2193 C8H1 7N3S3

2150 C9 H1 9NO2S 2194 C28 H5 7N3 02 S

2152 C9H2 1NS 2196 C6 H17N2OPS 3

2153 C N 120S 2197 C8H20 NO2PS

2154 C9H 21NS 2198 C 20H 29N 2OPS3

2155 CHI2 NO2S 2199 C6H 13NS

2157 c7H13N3S3 2200 C8H1 5NOS

2176 C6H1 5NO3S2 2201 c12H28N202S2

2177 C7H1 7 N03 S2 2202 C5H11NS 2

794

WR No. Molecular Formula WR No. Molecular Formula

2203 C6H15 NS 2228 C1 3H 27N306S2

2204 C6H1 3NOS 2229 C1 1H1 7N03S2

2205 C7H1 7NS 2230 C9 U1 3N03 S2

2206 C7 H15 NOS 2231 C9 U21 NO3S2

2207 C8 H1 7NS 2232 C1 4H1 6N2PdS2

2208 C8H1 5NOS 2234 C1 3R2 9 N02 S

2209 C8H2 0N2S2 2235 C1 6H3 6N2S2

2210 C9 H1 6N20 3S2 2236 C1 5 H3 3 NO3 S2

2211 C9lH10203S4 2237 C14H33N3S

2212 C1 H 18204S 2239 C 3H 30N2S2

2213 C7H1 4N2 S 2240 C1 1 H24 N2 OS

2214 C7 16N2S 2242 Ci 32N2OS

2215 Co H 8N204S 2243 CHi6 N2S2

2-16 C H 24N2S 2244 C6H1 5 N03 S2

2217 C6H1 4N2 S 2245 C1 2H2 7N03 S2

2219 C2 4H5 2N202 S2 2246 C1 0 H2 3 N03 S2

2220 C1 2H2 8N2 S 2247 C9H 21NS

2221 C i28NH32C2N4N308S4 2248 CH13 N30S

2222 C14H16C12N2Ni2S2 2249 C6H 15N3OS

2223 C 14U6N2NIS 2250 C5 H8N7,S2

2224 C2 8H3 2N6Ni 306 S4 2251 C7H N 2S2

2225 C3H9NO3S 2252 C5HI3N303S2

2226 C6H1 6N202 S2 2253 C2 0P3 0N3OPS 2

2227 C8H2 0N6 S2 2254 C2 7H3 6N3PS4

795

WR No. Molecular Formula WR No. Molecular Formula

2255 C7H18 NO2 PS2 2280 C4 H9 NS2

2256 C1 8H2 5 N2 PS4 2281 C13 NO S18 25 2 416'35 3 2

2257 C2 2 H3 3N2 PS3 2282 C6H N S22 332PS36 14 4 2

2258 C5 4H72 N9 P3 S6 2284 C7HI5NO2S

2259 C6 H1 8N3 OPS2 2285 C H 2N2OS22260 C 12H36N9P36 2286 C7H16N20S

2261 C28 H 48N2S 2287 C6H 3NO2S

2262 C61H29N302S 2288 C2H6N2S2

2263 C H 13NOS 2289 C 10H22N2S2

2264 CH18N2N02 S2 2290 C5 H 2N 2S2

2265 C10 H19NO4S 2291 C6H 214N2 S2

2266 C10H21N30 2S 2292 C1H1 23N0 2S

2267 C5141 9N3 43 2293 C6 H1 5N03S 2

2268 C6H 213N3 0S 2294 C 12H28NO3PS

2269 C H13NS 2295 C5H 2N203S2

2270 c5H11NS 2296 c 3H15N02S

2271 c 7H8N 2 S2 2297 C14 H31 NS2272 C7H N2S 2298 IH N7NS

6 83 3 2l 28 3'11

2273 c 6H 11N 3 S3 2299 c11H 17 NS

2275 C 6 H9NO02 S2 2300 CII1H 24 N2 S2276 C5 H13N5S 2301 C 11HN250NS

2277 C6H1 5NOS 2302 C2H 1 9N0 2S

2278 C8H6N2 02S 2 2304 C5 H 23NS

2279 C4H18N2S 3 22305 CH S36N204S2

796

WR No. Molecular Formula WR No. Molecular Formula

2306 C2 4 H3 6 N2 S2 2331 C6 Hl 2 N2 S2

2307 CIOH1 9 NS 2332 C9H 6N 2S2

2308 C H 17NS 2333 C3 H8 N2 S2

2309 C1 1H2 6 N- 2334 C1 6 H3 5 NS

2310 C1 3 H2 8 N2 S 2335 C1 4 H3 2 N20S

2311. C1 6 H3 6 N2S 2336 C5 H1 0 N4 S2

2312 C4 H1 3N2 PS 4 2337 C6 H1 6 N6 S2 Zn

2313 C6 H1 8 N3 PS 4 2338 C6 H16 CuN 6 S2

2314 C8 H2 1 N2 PS 3 2341 C7 H1 7 N03 S2

2315 C6 HI 3 NOS 2342 C H 13N 30 2S

2316 C7 H1 7 NS 2343 C7 H1 7 N3 0S

2317 C1 oH2 4 N2 S2 2345 C1 7 H3 7 N03 S2

2318 C1 4 H3 2 N2 03 S2 2346 C5 HIINO2 S

2319 C1 OH1 3 N02 S2 2347 CH 15N3S

2320 C1 2H1 5 NS 2348 C8 H2 0 N2 iS 2

2321 C7 H1 2 N2 02 S 2349 C8 H2 0 N2 PdS 2

2322 C7Ho102N2S 2350 C1 2 H2 8 N2 PdS 2

2323 CHI- 2 N2 02 S 2351 C]. 2 H2 8 N2 NiS 2

2324 C1 6 K3 5 N03 S2 2352 C1 6 H3 6 N2 NiS 2

2325 C3 H8 N2 0 3 S3 2353 C2 0 H4 4 N2 NiS 2

2326 CiIH8 FI 5 NOS 2354 C1 2 H2 8 CI 2 N2 N12 SZ

2327 C7 H8 F7 NOS 2356 C1 9 H4 1 NO3S 2

2328 C4 HgNO4 S2 2357 C7 H1 1 N03 S

2329 C8 H1 4 N2 S2 2358 C7 HI1 NO2 S2

2330 C2 H7 N3 S 2359 C H13 NO2 S2

797

WI. No. Molecular Formula WR No. Molecular Formula

2360 C8 H1 3 NO3 S 2386 C1 1 H2 5 NO3S 2

2361 C7 H1 1 NO3 S 2387 ClOH2 3 NO3 S2

2362 C2 0 H4 3 N03 S2 2388 Cl6H1 9 N04 S

2363 C1 0 H2 5 N3 S 2389 C4H11NO2S

2364 C4 H1 oN2 S2 2390 C1 2 H27NO3 S2

2365 C7 H1 2 N2 S2 2391 C9 H1 9 NS

2366 C4 H8 N2 S2 2392 C1 4 H2 7 NS

2367 C6 H1 4 N2 0S 2393 C7 H1 5 NOS

2368 C5 H1 0 N2 S2 2394 CloH2 1 NS

2369 C8 H1 4 N2 S2 2395 C1 oH2 3 N3 S

2370 C50H N2S2 2396 C1 1 H2 6 N2 0S

2371 C22H44N204S2 2397 C1 2 H 19NS

2372 C8H16N202S4 2398 C1 4 H2 1 NS

2373 C1 0 H2 6 N8 S2 2399 C2 2 H3 5 NS

2374 C9 H1 8 N2 02 S4 2400 C8 H1 6 N2 S

2-375 C5 H1 2 N2 0S 2 2401 C1 0 H2 1 NO3 S2

2376 C1 1 H2 2 N2 02 S4 2402 C H 23NO3 S2

2377 C3 H N 3OS 2403 C5 H1 3 N3 S

2378 C6 HI 6 NO3PS 2404 C1 2 H2 0 N2 S

2379 C1 2 H2 8 N2 06 S 4 2405 C1 3 H3 0 N2 0S

2380 C6 H1 5 NO3 S2 2406 C4 H9 N3 S

2381 C9 H2 1 N03 S2 2407 C5 H1 2 N3 S

2383 C818sN2$2 2408 C5H1 1 NO3 S2

2384 C1 4 H3 2 N2 S 2 2409 CI1H N 2S4

2385 C8 1 88NO2 S 2410 C6 H1 3 N3 S

798

WR No. Molecular Formula WR No. Molecular Formula

2411 CI3 H NO M 29032 2456 C10H15N 3S2

2412 C18 H3 9N03 S2 2459 C1 4H29 N3S3

2414 C8 H2 0N2OS 2460 C1 8H22N4 S4

2415 CIO0202S 2464 C1222 3F3NOS

2416 C802 SN203 2465 C9H 21NOS

2417 C5Hli02S 2466 C 11H17NOS

2418 C9H1 1NOS 2 2467 C1 1H1 7NO2S

2420 C1 2 H2 7NO 2468 C1 4 H2 9NS

2421 C4 H 31NOS 2469 C7H 7NOS

2422 C4 H1 2 N20s 2470 C3 H 9NS

2423 Ci 10 FS 2471 C7H1 5NO2 S

2424 C7 H1 1N02S 2472 C6 H1 7N3S

2425 C42?88N2S20 2473 C7 H15 NO5S2

2429 C10H13NS 2474 C6 H1 6 N2 S4

2434 C 30H 52N202S 2477 CH20N2OS

2435 C19 H4 0 02S 2478 C1 2 H1 6N2 S

2438 C7H1 3N302 S2 2481 C H 24N20 2S4

2439 C4H9NS 2494 C8 H20 N202 S2

2448 C11H15NO2 S 2495 C10 H24 N20 3S2

2450 C1 2 H1 6N20S2 2496 C7H1 7NO3 S

2451 C7 H 14N2 02 S4 2497 C11H2 6 N2S2

2452 C3 H 9NS 2498 C1 2 H8N206 S2

2453 C6H1 5N06 S3 2499 C1 2H24 N206 S4

2454 C7H1 7N02S 2501 Z1 2H2 6OS

2455 C7H 7NOS 2502 C1 1H2 7N03SSi

799

WR No. Molecular Formula WR No. Molecular Formula

2503 C llH 27NO2SSi 2560 C0 H 17NS2

2504 C4 V9 N3 S2 2561 C1 4 H2 2 N4 0 4 S4

2505 C1 3H16 N20 2S2 2562 C5 H1 1NS

2506 C7 13N30s3 2563 C6H oN2S2507 C4 H9NS2 2564 C7 H 1 5NOS

2508 H7 15 NS2 2565 C13 H 9 NS

2509 C6 H11 NS2 2566 C8 H15 NOS

2510 C6 H1 2 N2 S2 2567 C5 H1 3 N3 0 3 S2

2511 C4H9N3 0S 2568 C7H1 1N02S 2

2512 C8 H14 N20 2S2 2569 C11 H2 5N 3S

2513 C12H15N302S2 2570 C7H 7NOS

2514 C3 H NOS 2571 C1 0 H2 1NO3S2

2515 C1 0H1 6 N2S4 2572 C H23NS

2516 C3H9 N03 S2 2573 C6 16 N4S

2517 C8H20 N20 8S4 2574 C8 H NO2 S

2518 C9H13N03S2 2575 CNSH25NO2S

2523 C12H25 NO3 S2 2576 C1 4 H2 9NS

2529 C5H 12 N20S 2577 C 1033 N706S4

2539 C13H2 9 N03S 2578 C4 H1 3N20 3PS

2540 CH 13NS2 2579 C7H 5NO3S2

2541 C8 H ITNOS 2580 C 2 H2 7NS2

2542 C6H16 N20 2S2 2582 C5H11NS2

2557 C9H22 N2 0S2 2583 C7 H NOS 2

2558 C7 H1 3N03 S2 2584 C7H9NO2S

2559 C8 H1 3NS2 2585 C6 H1 0 02 S2

800

WR No. Molecular Formula HR No. Molecular Formula

2586 C4H7NS2 2631 C12H1 8N2 03S3

2587 C60 9NS4 2632 C1 01 1 4N203S3

2588 C 10H0N4OS 2633 C9 H1 7NS2

2601 C5H13NS 2634 C11 H1 6N20 3S3

2602 C1 2 1 6 2 03 s3 2635 C1 2 a2 21N20 3S3

2603 C4H7 NOS 2636 C10 13OS

2605 C9H11 N02 S2 2637 C8 H 19NS

2606 C15H3 4N2 S2 2638 C5R11 NS

2607 C10O~gNO7S2 2639 C9H19NS

2608 C12H2 6 N2 03S2 2640 C1 OH2 1 NS

2609 C8H105NO2 2 2641 C7H15NS

2610 C8o 1 1N03 S2 2642 C7H1 5NS3

2611 C60 9NO2 S2 2643 C8 H1 8N20S

2615 C6H1 4N4 02 S2 2644 C3H9NO2S2

2619 CR6HlN302S2 2645 C6014N404S2

2621 C8H20N208 S4 2646 C10 N2 2N406 S4

2622 C6H1 3NO2S2 2647 C1 0H24 N20 6S4

2623 C3 H9 NS2 2648 C7H1 5 NS

2624 C8H 19NO2S 2649 C6H 13NO 3S2

2625 C6 H1 3N305 2650 C5 H1 3NO3S2

2626 CI3H1 7N04 S 2651 C1 0 H2 4N206 S4

2627 C7H1 5N30S 2652 C4 H1 0N20 3S2

2628 C10 U1 5NOS 2654 C1 3H2 1N02 S

2629 C1 9H3 1N02 S2 2658 C11 H2 5 N03 S2

2630 C13H20N20433 2659 C9H21 N03 S

801

Ut No. Molecular Formula WR No. Molecular Formula

2660 C101_93 2703 C1 sH3 3NoS

2663 C4 a8Fe. 2S2 2704 C4 BlNSý,

2664 CH 1 7NO2S 2705 C9 H 3NS2

2665 C7H1 8N2 S2 2706 C1 1H24 "20 3S2

2666 C9H2 2N2 02S2 2707 C 11H 16N 20 3S2

2675 C U321NO3S 2708 C5HS12N2032

2676 C4H1 2N2s 2 2709 C H 25NO 3S2

2677 C7015NO4S 2710 C8H11NS2

2686 C10? 1 3 NS3 2711 C2 4H26 N2OS

2687 C11B17NS2 2712 C4H7NO2S 2

2688 C1 2H1 9N02S 2713 C14H26 N20 2S4

2689 C10 H11NOS 2 2714 C13? 24 N202 S4

2690 C10 2 3NO3 S2 2715 C9 H2 2N2S2

2691 C1 2B25No3S2 2716 C1 1 H26 N20 6S4

2692 C1 7H30N2S 2717 C4 H1 2N20 6S4

2693 C4H12N2S 2718 C4H1 2N20 2S2

2694 C4 H NO2S2 2719 C9 H2 0N402S2

2695 C2H7NO2 Se 2720 C6 H 15NS

2696 C1 2H28N2 S 2721 CH O5N203PS

2697 C11H2 2 N20 2S 2722 C8H19 NS2

2698 C9 H1 3NS2 2723 C9H13NOS 2

2699 C10 H2 0N20 3S3 2724 C5H1 2N20 2S2

2700 C1 6H1 8 N20 3S2 2726 C6 H1 4N20 3S2

2701 C9H2 2N2OS2 2727 C6H1 4N20 3S2

2702 C8H1 0oCNS2 2728 C14H2 3N07S

802

WR No. Molecular Formula WR No. Molecular Formula

2729 C1 3R2 1M30 7S 2818 C60 1 5NS2

2732 C1 2H27NSSe 2819 C60 1 6NO3 PS

2734 C6H1 3"O2S 2820 C5 U9N3 S

2738 C7B1 4N20S3 2821 C5B9 NOS 2

2739 C1 2H1 9 N03S 2822 C6H1 7N203 PS

2742 C1222N2 03S2 2823 C7H19N20 3PS

2743 C1 2H18 N2 03 S2 2824 C821N203PS

2744 C12 H1 9N04 S2 2825 C80 2 oN2 S2 ZN

2745 C4B8 F3NS 2826 C10 H2 4N2PdS2

2750 C1 3? 30 N 2 02 S2 2827 C80 14 N2Ni 204 S2

2752 C8HI 0N202 S2 2836 C6 H1 2F3NS

2753 C5H13502S 2837 C1 7 H3 7N3S

2754 C1 2H1 9"0 3 S2 2838 C1 8143 7N3S3

2755 C1 6BH19 N03 S2 2839 C9R1 7 N30 3S2

2778 C1 3H9 NS2 2840 C9 R1 3 NOS 2

2801 C8 H2 0 N60 2S2 2841 CH4 02s

2802 C7H1 N2S2 2842 C8H102S

2803 C11H2 3NOS 2844 C1 2H19 NO6 S

2804 C1 1H1 6 N20 3S 3 2845 C1 01R1 5 N04S

2806 C7H13NO2 S 2846 C6H15NO3S

2813 C1 7H21 N04 S2 2847 C8 H20 N2 S2

2814 C1 1H18 N2S 2648 C5 H1 2N2 03S2

2815 C10 H2 4 N2S 2850 C1 4H2 9NO4 S2

2816 C7H1 7NOS 2851 C1 4H31N04S2

2817 C H 21NS2 2852 C2 H606S4

803

WI Wo. molecular PFommla W, No. Molecular Form••a

2853 C2H7NSe 2905 C611 5306S2

2854 CsH19NOS 2906 C1 3H2 7 "03S2

2855 C1 0B23NOS 2907 C 12H 27NO4S2

2856 C8? 19 N03S2 2908 C1 1H25N04 S2

2857 C1 3H2 7NO4 S2 2909 C1 2lH2 7N04 S2

2859 C10 H2 2N202 S 2910 C3H9 NOS

2860 C160 2 8 M2 86 2911 C7H14 N2 S2

2861 C6 H1 4N20S 2916 C1 1H1 7N303S2

2862 C8H20 N20 3S2 2917 C4H1 1 N05 S2

2863 C7H1 7NOS 2918 C10H21NO5 S2

2864 C9 H19 NO3S2 2919 C2 0H3 9N03 S2

2865 C10H2 3NO4 S2 2920 C2 1H2 7NO3 S

2866 C14H2 9NO3 S2 2922 C6H10 F5 NOS

2867 C8 Ro0 C1NS 2 2924 C1 3B2 4N20S2

2868 C1 3H29 NO3 S2 2925 C1 2H2 2N2OS4

2869 C10H24 N6 02 S2 2926 C1 1H2 5NO3 S2

2870 C14H28N604S2 2927 C1OH2 INS

287] C1 5iH 3 1NS 2928 C7H1 5N02 S

2872 C3 H 27NS 2929 C H 21NO2S

2873 C H 26N202S 2930 C6H9NOS2

2874 C8H 17NO2S 2931 C 19H 24N6S3

2875 C7H15 N02 S 2932 C6H1 6N20 6S4

2888 C5 p141 NO2S2 2933 C6H1 6N20 6S4

2889 C14H20 N20 4S4 2934 C8H20 N20 6S4

2904 C15H1 4N20 3 S2 2935 C7H 18N206S4

804

WR No. Molecular Formula WR No. Molecular Formula

2936 C9 H2 2 N2 06 S4 2981 C5 H1 2 N2 04 S2

2937 C1 2 H1 5 NS 2982 C5 H8 N2 S

2938 C7 H1 0 F 7NOS 2983 C1 5 H32N6S3

2939 C8 H1 9 N0 5 S 2984 C1 2 H2 8 N6 02 S2

2940 C1 70 2 9 NS 2985 C1 0 H2 4 N6 04 S2

2941 C1 3 B 2NO4$2 2986 C5H 13NO5S 2

2942 C1 1 B2 3 N0 3 S2 2987 C1 0 H2 4 N2 02 S2

2943 C8 H1 ON2 02S2 2988 C1 0 H2 4 N2 08 S4

2944 C9 H 13NOS 2 2989 C 5H10F3OS

2945 C17 H29 S2 2990 C1 4 H2 9 N04 52

2946 ClN20 3'2 2991 C1 2H2 7N04 S2

2947 C7 H1 6 N2 03 S2 2992 C4 H7 N04 S2

2948 C7H15N05S2 2993 C1 3 H1 9 N03S 2

2949 C1 1 H2 3 NS 2994 C5H1 3NOS

2950 C1 3 H2 7 NS 2995 C1 9 H2 2 •NOS

2951 C1 2 H2 7N0 2 S 2996 C2 1 H2 9 N03 S

2964 C1 0 H2 4N2 0 2 ' 2 2997 C5 H1 3 NO4 S2

2965 C1 0 H2 4 N2 08 54 2998 C8 H1 7 NO7 S2

2968 C7 H1 7 N0 6 S2 2999 C8 H1 6 N2 04 S2

2969 C17 N04 S2 3022 C1 1 H2 3 NOS

2970 C9H21 NO4 S2 3023 C2 4 H4 8 N2 S2

2971 C1 0 H2 3N04S2 3024 C1 3 H2 9 N05 S2

2972 C1 2 H2 5 NO4 S, 3025 CeH Ns2 04 S2

2973 C1 3 H2 7 N04 S2 3026 C6 H1 2 N2 S

2974 C2 4 H5 2 N6 04 S2 3027 C1 6 H1 6 N2 S

805

Vi No. MlscuLar Formula Wi No. Moltcular Formula

3028 C1 8 U2 9 O3 S2 3079 C6 H1 0 N2 04 S2 Zn

3029 Cs87C1302S2 3080 C6H 10 2 NIO04 S 2

3030 C811NO3S3 3081 C6 H1 2 N2 04 PtS2

3036 C1 1 "1 6 02 S 2 3082 C9 H1 8 CoN3 O6 S 3

3037 C8 89 NS 3 3084 C6 H1 2 F3 NOS

3038 C7 H1 4 F3 NOS 3085 C1 0 H1 7 NO3S3

3050 C1 3 U2 1 NO4S 2 3086 C1 3 H2 1N03 S2

3051 C6 H1 3 NS 3087 C1 3 H2 1 N0 4 S2

3052 C6H1 5NO3 S 3088 C4 8H11 0 N1 2 S2 4

3053 c4H12N202Se2 3092 C6 H1 0Cd2N2 04 S2 ....

3064 C4H1 2N20 2S 3093 CT7 H 17NO5S2

3065 C5 12N2S 3094 C7H1 8N2 02S

3066 C8l20N202S 3095 C5 13NOS42

3067 C1 9B31No3 S2 3096 C9 B1 4F7NOS

3068 C1 7 H1 6N2OS 3097 C101H24 N202 S2

3069 C1 1H23N04 S2 3098 C8 H1 6N2 0S

3070 C1 1H25 N04 S2 3099 C H 20 N2042

3071 C10H14C1N04S2 3100 C7H1 8N20S

3072 C1 4H2 3NO6S2 3114 C7H1 5NS3

3073 C1 0H2 4 N2NiS2 3115 C6 H1 5NO2 S2

3074 C1 0H24 N2NiS2 3117 C6 H 13NO S2

3075 C1 2H28 N2NiS2 3118 C1 7H19 N303S2

3076 C8H1 4N2NiS2 3119 C5 H7 NO2S5

3077 C9H16N2 Nis2 3120 C8 H1 4 F5 NO2 S

3078 C1 2 H2 2 N2 Nis 2 3122 C1 2 H1 7 C1 2 N0 4 S 2

806

WK No. Molecular Formula WRNo. Molecular Formula

3123 C8 H2 0N20 2S2 3232 C1 2 H2 5N02 S

3124 C4H11NO4S2 3233 COHI15NS

3125 C1 9H2 3 NO3 S2 3235 C1 OH21jN0 3 S2

3134 C18 27NO4S2 3236 C1 3H2 7N 4 S2

3135 C I3 H19 1N2 S 3237 C1 1H1 7N04 S2

3137 C1 4 H3 4N4 02 S2 3238 C13 H2 7NO3S2

3138 C4H1004S2 3239 C2 0 27N05S2

3139 C8H1 8OS3 3240 C1 2H19 N 5 2

3140 C2H7 NOS 3241 C8 H1 9NOS

3147 C1 4 H2 3NO4 S2 3243 C10 H1 4 N2 S2

3148 C1 0 H2 2 N2 S 3244 C1 0H1 5N02 S2

3149 C1lH 2 4 N2 S 3270 C5H10 N20 3 S2

3150 C H 29N3S 3271 C 20H 25NO4S2

3151 C1 4H2 7N3S 3272 C10 H2 3N02 S

3152 C1 1H2 4N2 S 3273 C6H15 NO6 S2

3153 C1 1H2 1 NS 3280 C11H18 N20 3 S2

3154 C1 1H1 5NS 3281 C2H8 N2 02 S

3155 C H 21NS 3282 C1 9H2 3 N3 0 3S2

3156 C 11H21NS 3283 C6H1 7N20 3PS

3157 C4H 34N402S2 3284 C H 20N303PS

3158 C7H1 8N204S2 3285 C 23H 31NO 4S2

3200 C19H2 9N03S2 3286 C9 H1 8 N2OS

3201 C 14H32N2S 3288 C9H 19N03S2

3229 C1 3H1 7N03 S 3289 C6H1 4 N204S2

3231 C20H23N03S2 3290 C6H12N203S2

807

Vi No. molecular Formula WR No. Molecular Formula

3291 C11H1 4N2 03 S, 3319 C8H1 6 N20 3S2

3292 C8 H1 3NS2 3325 C2 1H2 7N03S3

3293 C14H2 3 NOS 3326 C1 2H30N40 2S2

3294 C8 H1 4N2 04S2Zn 2 3331 C40 H8 4N204 S2

3295 C8 H14 Cd2N204 S2 3332 C4 0 R8 0N204S2

3296 C4H8ClNO2Pd 3333 C 40H8 4 N202S2

3297 C7B1 7 NO 2S 3334 C4 0 H8 0N206 S2

3298 C1 1 H2 3 N03S 2 3335 C1 3H1 8 F3N04 S2

3299 C1 2H1 9N04 S2 3336 C14 H2 3N04 S2

3300 C1 2H19NO4 S2 3337 C14H2 3N03S2

3301 C1 2H1 9NO4 S2 3338 C 14H 23NO 5S2

3302 C1 3R2 7NO3S2 3339 C14H2 9NO3 S2

3303 C2 2H31NO7S2 3340 C H 23 N3S2

3304 C14 h20 1rNO5 S2 3341 C11H2 3N03S2

3305 CI N019 4O S 3342 C4H NOS4.19 2 1423 3 2

3306 C7HA6N3OS 3343 C1 4H2 3N04 S2

33C' C1OH1 4CINOS 3344 C2 8H6 2N4 S2

3308 C7H1 6E2 03 S2 3345 C7H1 7N03S

3309 C6H11 NOS 3346 C2 0H4 6N4 02S2

3310 C1 8 H2 2N3 03PS 3347 C1 4H3 4N4 04 S2

3311 C6 H1 4N03 PS 3348 C1 2H2 8N2 04 S2

3312 C1 6H3 3NO3 S2 3349 C6H1 3NS

3313 C14H 23NO3 S2 3350 C1 2H2 6N4 08 S4

3317 C6H11N02$2 3351 CH 20N202S3

3318 C9 H19 N30 3S 3352 C H NO 2S

808

WR No. Molecular Formula WR No. Molecular Formula

3353 C8 H2 0 N2 0 8 5 3542 C5 H1 1 NS

3354 C H 15NS2 3543 C4H8N2S

3355 C 5H1NOS 3547 C6H 6NO2PS2

3356 C6H1 5NOS 3548 C 11H 17NO 3S 2

3357 C20 H2 5N03 S3 3549 C H 17 N3S2

3358 C1 2H2 7N03 S2 3550 C12 H1 9N03S2

3359 C9H11N 3S2 3551 C1219 NO3S2

3360 C1 0H1 1 N05S2 3552 C8 H1 1NO3 S23361 C11H15N05S2 3553 C5 H NO S2

3423 C12H25N04S2 3554 C 8HONO5S23426 CH5NO 4 S2 3556 C8H1 7N303s

3427 c13H21N03S2 3557 CN17ONO3S

3428 CI13 H26 N2 S 3558 c 14 H29 N03 S23429 c 14Hs 2 3559 C6H 16N2c4S2

3431 c12H19NS2 3560 c 16H25NO3S2

3432 C1317N02S 3561 C13H27NO3 S2

3433 C1 2H219NS 3562 C1 2H 2 5NO3S2

3424 C5H13NOS 3563 C 26H 51NO S2

3435 c7H17NOs2 3564 C14H 29 NO3S 2

3436 c7H17N 4$2 3565 C1 4 H23NO4S 2

3537 C1H 8N203S2 3566 C 16H31NO32

3538 C9H1 1NS3 3567 C1 4H2 9NO4S 2

3539 C14H2 9NOS 3568 C1 0H24N204S 2

3540 C10H1 5NOS2 3569 C5H 13N0 5S2

3541 C21H35N03S 2 3574 C1 0H15N03S 2

809

WRI No. Molecular Formula Wi Noý ,olacular Formula

3575 C9 13 O3 S2 3623 C8H1 6 C1NS3583 C 11R 17NOS 3624 C8H1 6 CINOS

3584 C.1H 1 3 N02S2 3629 C4H1 2N20S 2

3596 C6H12N2 S3 3679 C6H16 NO3PS

3597 C7H 15NO5S2 3680 C9 17N07S2

3598 C7H1 5 N3 02 S 3681 C1 4lH2 7N07S2

3599 C7H15N305S2 3682 C8H17N04S2

3600 CI12 H26N 40 2 S2 3683 C 10HI13No04 S2

3601 C 10 R20 N20 4 S2 3684 Cl11H 12 N20 3 S23602 C65HNS3 3686 C8H1 7N303S

3603 C7 H 13NS 3687 C 13H NO 2S2

3604 C6 H NOsS2 3688 C6 H N3S

3605 C1HS23N04S2 3689 C6H1 7N20 3PS

3606 C 14 H32 N20 6 S2 3690 C5H 12 NO 3PS 23607 C7H1 7NO6S2 3691 C7 H NS2

3608 C6H154c3S2 3692 C H 10N 2S

3609 C 14H 20N23S2 3693 C12H19N30S

3610 C14H29N04S2 3694 C7H20N206P2S2

3611 C18H29N03S2 3695 C H 24N206 P2S2

3612 C18H35N03S2 3696 C1OH26N206P2S2

3613 C1H23NO3S2 3698 C 10H 21N2S

3614 C13H27N04S 2 3699 C8H 16N202S3

3615 C8 H16 N02S 3819 C 12H 18CINO4S2

3617 C H 15NO 5S 3820 C 24H35N5S2

3620 C H C1N0 S 3821 CSH3NO

18 293 2 3 C 2 34 2 2

1123 3 369810210

WR No. Molecular Formula WR No. Molecular Formula

3822 C3 H21N0482 3851 C H NO 2S

3823 C.IH15N03 S2 3852 C10 H2 2N40 2S2

3824 c13 H27N 3 S2 3853 C8H1 7NOS 2

3825 C1 5H3 1 N03 S2 3854 C6 H1 3 NS3

3827 C 28H43NO7S2 3855 C 16H NC2S

3G28 C1 5 H2 5 NOsS2 3856 C1 3 H2 0N2 03 2

3829 C2 0 H3 5 NO32 3999 C10 H2 3NOS

3830 C 13H 21NO582 4100 C 5i 1NS3

3831 C 154 31NO382 4101 C3 H 1NOS22

3832 C1 5 H2 5 N05 S2 4102 C1 2 H1 9N045 2

3833 C H NOS 4103 C 1423 NO42

3&34 C 3 H NO 142S3634 C24 H5 NO3 4104 C1 2H2 5N03S2

3835 C10 H2 4N20 4 S2 4105 C1 6H3 : N 3S2

3836 C8H15N0782 4106 C2 H 1CNO 4S2

3837 12H23N 7 S2 4107 C1 4 H2 9 N03 2

3838 C12H23P0782 4108 22 H1112NO582

0d39 C7H15 NO5S2 4109 C1 3H2 1N04S 2

3840 CHNOS 4110 C2 4 H35 N07S2

C10H19N05 2 4110 7

3841 C8H 18N204S2 4111 C H 23N4 S2

3842 Cl8HlqNO5S2 4112 C6H 14N2042

3844 C6H1 5 N02S 4113 C4 H8 N2 S

3845 C7H1 8N20 4S2 4114 C. 12H19 N03 2

3846 C24 H5 4N4S2 4115 C1 1 H2 4 N2 8

3849 C3'I7NS3 4116 C4 H1 1 NOS 2

3850 C5H11N3 4117 C6 H 5NOS

811

WR No. Molecular Formula WR No. Molecular Formula

4118 C1 0 H1 5 NOS 4438 C1 5 H3 3 N3 S

4120 C7 H1 2 N2 OS 4439 C1 2 H2 7N3 S

4121 C18HI6N206S2 4440 C1 3 H 29N303S2

4122 C6 H 6NO PS 4441 C1 5H3 3N3S

4123 C6H 15NO3S 4442 C 15H 33N303S2

4242 C6H9N02S2 4443 C1 1H2 5N3S

424. C4H9N02S2 4444 C1 3H27N04 S2

4244 C5 H1 0N2OS 4445 C1 3H2 7N04S2

4245 C OH20N203S2 4446 C H N29N4S2

4259 C10H26N2010P2S2 4447 C1 2H1 8N206S2

4282 C7H1 8 N205 S2 4466 C5 H9NO2 S

4283 C2 2H4 6N4 S2 4467 C6 H 12N 2OS

4312 C7H17 N3S 4468 C3H1 0NO3PS

4333 CHI1 N203PS 4469 C3H1 0 NO3PS4376 C7177N303S2 4470 C4 12NO3PS

4381 C H 5IO3S 4471 Csl NO03PS10 15' 33 5 112 3

4428 C6H1 3N035;9 4472 C6H16NO3PS

4429 C5H11N 3S2 4473 C5H1 2NO5 PS

4430 C10 H22 N402S2 4474 C6H14 N5PS

4431 CSH22 N206 P2 S2 4475 (1 H2 0NO PZ

4432 C11H24N203S2 4476 C12 24

4433 C6 H1 3N05 S2 4477 C1 2 H24 N07z..

4434 C9H21N 3 03 S2 4478 C1 8H3 2NO7PS

4436 C H 29N3S 4479 C8 H18NO4 PS

4437 C11H25N 3 03 S2 4480 C1 2H2 4NO4PS

812

WR No. Molecular Formula WR No. Molecular Formula

4481 C 12H 24NO4PS 4556 C7 15NO3S

4482 C1 4 H2 8 No 7PS 4611 C80 1 9 N02 S

4483 C1 8 H3 1 N07S2 4612 C1 7H2 2 N2 0 2 S2

4484 C1 2 H2 3 NO 4 S2 4614 C6 H1 2 N2 03 S2

4485 C12 H1 9 N07 2 4615 C 4 N 0 s12 1 7 24 11 3 3 2

4486 C1 4H2 7N07S2 4616 C 12H 25 30s

4487 C1 0111 9 N0 2 S2 4617 C2 0 H2 8 N2 S4

4534 C1 2 H2 8 N2 03 S2 4618 C2 8 H4 1 N3 05 S2

4535 C 11H 21NO3S2 4619 C5H 13NO3S2

4536 C 16H 33NO3S 2 607H 15NO 3S156 C6H3303S2 4660 C7 H1 5 N03

4537 C1 8 H2 9 NO4 S2 4700 C 14H 14S3

4538 C1 4 H2 9 NO4 S2 4701 C OH15 N4S2

4539 C15H31N 3S2 4703 C 1H23 N02S

4540 C1 4 H2 9 NO4 S2 4707 C4 H9 NO3 S

4541 C1 2 H2 5 N0 4 S2 4747 C9 H1 9 N03 S

4542 C1 4 H2 9 N0 4 S2 4758 C1 1 H1 9 N0 3 S3

4543 C1 4 H 17 NO4 S2 4769 C1 4 H2 3 N0 4 S2

4544 CI6H33 NO4 S2 4772 C4 H1 1 NOS

4545 C5 H 31NO4S2 4774 C9H 1NO5S2

4546 C14H23 NO4S2 4777 C H R25N4S2

4547 C1 2 H1 9 N0 4 S2 4781 C 14H 29N4s2

4548 C1 4 H2 3 N0 4 S2 4782 C 12HNO 5PS

4549 C1 6 H2 0 N4 04 S4 4783 C1 5 H2 5 N04 S2

4553 C12 20N2 02 S2 4786 C1 6 H2 2 N3 04 PS

4555 C12 H24N203S2 4788 C1 4 H2 3 N04 S2

813

"VR No. Molecular Formula Vt No. Molecular Formula

4790 C1 3R2 0 N05 PS 5033 C1 2 H2 1 N03 S3

4792 C1 2H1 8 CIN0 4 S2 5034 C5 H 9NO2 S2

4793 C1 2H2 6 NO5PS 5035 C12 H2 3NO3 S2

4794 C8 H1 4 NO5 PS 5041 C 1H 1NS

4795 C9 H2 0 N05 PS 5045 C1 1 H19NS

4797 C9H2 0NO5PS 5132 C1 oH2 1N03 S

4798 CsHI 3 F5NO5 PS 5133 C9Hl9N02S

4799 C7H1 3 F3NO5PS 5134 C H 21N3S2

4805 C4 H 23NO4S2 5135 C 14H 34N406S4

4808 C1 2 H2 5NS 5136 C6H1 1NO3 S3

4845 C6 H 13NO3S2 5137 CH 14NO3PS

4853 C2 0 H4 4N204 S2 5138 C7H1 4N203 S24917 C6H11N02S2 5139 C oH15NO4PS

5019 C 9H 19NO 5S 211C 22H 32N2S401C91I9 5s2 5141 C22322S4

5020 C11H21 N5S2 5142 C8llN03S25021 C8H15N05S2 5143 C1 1H18 NO4PS

5022 C8H13N05S2 5144 C7H1 9N2 03PS

5023 C8H 2 OS 5145 CsH NOS

5024 Cq2H2 0 N303 PS2 5146 C1 1 H1 7NO3S3

5025 C1 0 H2 3U02 S 5332 C1 1H1 7NO4 S2

5026 C oH23NO2S 5803 C9H 9NOS

5027 C20 H4 4 N2 04 S2 5804 C12 H15 N02S

5029 C5H1 3N3 S2 5805 C8 H1 5 NOS

5030 C H 9NO2 S2 5806 C1 2 H1 7NOS

5032 C5HgNOS 2 5807 C H 34N2S2

814

WR No. Molecular Formula WR No. Molecular Formula

5817 C1 5 H3 2 NO5 PS 6132 C1 4H1 3 C1N2 0 2 S2

5818 C 17H 36NOPS 6133 CR4 NO2S

5819 C1 1 H2 2 NO5 PS 6134 C1 2 H1 9 NO5 S3

5820 C7H15N05S2 6135 C11H23NO3$2

5821 C1 7 H3 5 N0 5 S2 6136 C13H27NO3S2

5822 C1 3H1 9 105 S2 6137 C1 4 R2 3 no4 S 3

5855 C5 H1 0 N2 0S 3 6138 C1 3 H2 1 NO4 S 2

5879 C7H15N 3 S2 6139 C1 3 H2 1 NO4 S2

5935 C4 H2 N2 S2 6165 C8 H1 9 NO5 S 3

5936 C6 H6 N2 S2 6262 C1 4 H2 2 NO3 PS

5937 C1 6 H1 4 N2 S 2 6298 C1 0 H2 1 NO 5 S 3

5938 C8 H1 0 N2 S2 6306 C1 5 H2 5 NO6 S

5979 C12H19 NO4S2 6307 C8 H9 NO4 S2

5980 C1 2 H1 7NO3 S2 6309 C8 H 8N 20 6S2

5981 C12H18 rNO4S2 6310 C1 0 H12N20 8 S4

5982 C oH gN0 3 S2 6311 C8 H8 N2 06 S2

5983 C1 3H21N04 S2 6312 C9 H1 1NO4S 2

5984 C1 4H29N03S2 6313 C10H1 3NO4 S2

5985 C1 3H2 1N04 S2 6314 C8H8 BrNO4 S2

5987 C1 3 H2 7NS 6315 C6 H1 4 NO5 PS

6120 C1 0 H1 6 N2 03 S2 6316 C7i16NO5PS

6128 C14 H2 3N05S3 6317 C9H2 0NO6 PS

6129 C1 2H1 9NO5 S3 6318 C1 3H2 2NO5 PS

6130 C1 6 H1 6 BrNOS 2 6347 C H 17NO S3

6131 C1 0 H1 2 BrNS 2 6364 C16N2S

815

UR No. Molecul.ar Formula, WR No. Molecular Formula

6365 C7H18N2S 700C C10 U2 3 N05 S3

6366 C1oB16N2 03 S2 7454 C10 51 6N03p3

6367 C8 H1 7N3 02S 7455 C1 3B2 0NO4PS

6368 C2 2H32 N2 02 S2 7457 C1 2HH3 F1 2 N05 S2

6369 C11H1 7NS2 7466 C1 3H 27NO3 S2

6370 CllH1 8NO3PS2 7467 C14 H2 9 NO3 S2

6371 C7H1 5N04 S3 7468 C1 2lH1 8 CINO3 S2

6372 C10 H1 1N03S3 7470 C7H1 4N204 S2

6373 C1 1H1 3NO3 S3 7471 C2 H3NO3S2

6374 C1 0 H12 N2 03 S2 7472 C1 1H1 6 BrNO5 S3

6375 C11H14 N2 03 S2 7766 C2 1H2 5NO5 S

6376 C8H16 NO5 PS 7767 C14 H15NO5 S

6399 C7H14N203S2 7982 C H 23NO5S3

6400 C14 H2 9N03 S2 7983 C H 21NO 5S3

6401 C H NO4S 8049 C1H2NO5S13 21 4 2 804 C 5 H 34

6402 C13H27N 3S2 8053 C7H8N2S2

6403 C13 H27N 3 S2 8161 C10 H1 4N204 S2

6404 C13H27 NO3S2 8164 C1 3H2 1NO05 36456 C1 2H2 4N2 04S2 8165 C7H 1 7N03S2

6458 C5H13N204PS 8186 C4 H1 2NO4 PS

6656 C7 H 1 7NO5S3 8187 C5H1 4NOs5 PS

6799 C2 2H2 7NO3 S 8188 C2 8H5 5 NO3 S

6923 C1 2 H18N206S3 8189 C8 H1 5N03 S

6924 C6H1 3N05 S3 8191 C20 H4 0 N204 S2

6999 C1 5H2 5 N05S3 8192 C5H1 4 NO4PS

816

WR No. Molecular Formula WR No. Molecular Formula

8308 c 26 H43 NO5 s 9053 C 25 H39N4 0 3PS

8309 C 9 1 NO 3S3 9054 Cl8i 1 NO205PS

8310 C 11 H16 ClN05 3 9055 C 1 H 26N 40 3S2

831 c13 H21 NO5 2 9056 C 9 H20N 20 5 s2

832 c10 H14 N2 03 s3 907c 9 R21N 30 4 s2

8313 C 10H17N03S3 9058 C 9H 21N2 0 5PS

8314 C 12 H18 C1N04 s2 9059 CU 20 N02 PS 2

835 c11 H23 NO3 2 9061 C 7H 18 N02PS 2

8316 C 1 H 16NO204S2 9062 c1 0H22 N0P"S

8317 C 11 H16N 20 3 s3 9063 C 13 H28 NO5PS

8361 C 12 H15NO 2S2 9064 c1 2 H20 N 30 4PS

8362 C 10 H16 N03 PS2 9069 C i H2 6N3 0 4PS

8363 C 8H 10N 40 3 S2 9070 c2347 5S2

8364 c9 H12 N4 03 2 9071 c1 7N

8365 C 10 H24N 20 6 s4 9088 c2 3H4 3 N05 s

8366 C H N S 9089 C H NO S14 34 42 8 19 2

8367 c HNO NS 3 9090 C R 3 NO8S

8368 C 12 H29 N 20 3PS 9091 37H7NO1s

8369 C 13 H31 N 20 3PS 9092 C 2 H 31NO 8S

8439 C 12 H18 C1N05 S 3 9093 C 10 H17 N03 S3

8629 C 7H 17 N05 s3 9094 183N34S

8713 c 6 H18N 20 6 p2 S2 9095 C 9H 19 NO3 s2

8782 C 12 H25 N05 s3 9096 C 13 H27 NO3 s2

9051 C 12 K3OS3 9097 C 1 H 20NO203S3

9052 C 2 H 48NO 5PS 9462 C 1 H 18NO203S2

817

WR No. Molecular Formula WR No. Molecular Formula

9463 C1 4 H1 80204S2 25098 C1 7H3 6 N20S2

9528 C1 1H2 5NO3 S2 25099 C4 H8 N2S

9575 C 11H 22N 203S2 25126 C H13N303S2

9716 C13H30N203S2 25127 CS 1 22N20 3 S3

9717 CH 1 8N20S4 25176 C 16H 27NO5S3

9718 C2 2 H2 6 N4 S6 25210 C1oH22N2S

9719 C8H1 7N3 02 S 25211 C7H1 oN2 04 S2

9720 C H14N203S2 25212 C 14H 29NO3S2

9721 C6Hi3PO4S3 25329 C 21H 25N3OS29722 C13 H 19N302 25330 C15H519N3052

9723 C H 18NO5PS 25331 C 15H 31NO4S2

9724 C13H19N305S2 25416 C11H165CIN5S3

9725 C H 30N402S2 25417 C H 17NO5S3

9766 C 1820N 2S 25422 C6H1 4 O 2 S

9767 C23H25NO3S 2 25871 C H 25NO3S

9768 C19H3 PO 3 S2 25872 C10H22NO4PS

9839 C1 8H31N0 5S3 25875 C 14 H23NOs2

9840 C H 4N2 03S 25876 C 12H 9NO 5S2

9841 C15H14N203S 25877 C7H9N20 3PS

9842 C 16 H15NO3 S 25878 C 6 H16N 20 3 S215504 C2 H 6OS 25879 C H 25N302S

17637 C17HH810S3 25880 C1 4H36N406p2S 2

19635 C6H 14 02 S2 25881 C1 5H22N303PS

22047 C2 HN3S2 25882 C1H94N203S3

25077 C H 24NO5PS 25883 C6HI6 N203S2

818

WR No. Molecular Formula WR No. Molecular Formula

25884 C8HllN3 03 S2 27077 C8 H2 0?10 5 PS

25885 C1 5 H2 0 N2 04 S2 27286 C1 8 H2 0 N2 0 2 S2

25897 C12 28 4 03 S2 27388 C1 1 H1 4 N2 0 3 s 2

25898 C8iH 9N303S2 27389 C2 0R2 80403S2

25899 C3 H 28N404S2 27390 C6 H11 N205 PS

25900 C13 20442 27391 C2 3H50 N304 PS25901 C15H24N404S2 27392 C 24H 52N4PS

25902 C1 3H29 N4 04Ps 27393 C20 H2 9N4 03PS

25903 C9 H1 4NO3PS 27394 C1 7B2 3N404PS

25904 C8 H2 0 N3 0 3 PS 27395 C1 9 H2 7 N4 0 4 PS

25905 C1 5H3 1N40 4PS 27396 C18H40N206S2

25906 C1 3H2 1 N40 4PS 27544 C8E11 N303 S2

25907 C15H2 5 N4 04PS 27631 C2 0H3 5NS2

25930 C14 Hs1 N2 04 S2 27632 C2 0H3 2N2 S2

25935 C9H7NO5S2 27633 C5 H1 1NO3S2

26125 C1 1 H2 4 NO4 PS 27656 C 6 H2 5 NO3 S2

26169 C9 H14N2 OS 27657 C1 3 H2 1 N5 05 S 2

26330 CH 13NS 27658 C1 1 H1 7 NO3S3

26331 C7 H1 7NS 27716 C9 H1 8 N2 0 3 S2

26332 C8H 15NO2S2 27730 C9 H 20N s

26723 C2 4 H4 4 N2 0 4 S2 27736 C8 H2 0 N05 PS

26904 C8 H1 2 N2 04 S2 27737 C2H 6N 20 3S4

26934 C1 9 H3 3 NS2 27738 C9 H2 1 N03 S

26935 C2 0H35 NOS 2 27739 C1 1H1 3NOS 3

26936 C19H3 2 C1NS 2 27740 C6 H1 1N0S 3

819

W INo. molecular Form.la WR No. Molecular Fonsrla

27748 C1 3H2 9NO5S2 30462 C2 6R5 6N204S2

28350 C10 H1 1 3S2 31870 C10 R17NS2 Si

28444 C12 H2 6N4 02S2 31893 C1 4H2 3NOS

28445 C26H4 8N6 04S2 31894 C11 R2 3NS

28446 C14H30 N4 08S4 31896 C11H23NS

28447 C1 4H2 2N2205 S2 31899 C1 0 14N204 S2

28448 C1 3 H19BrN20582 32061 C1 2H29 N40 3PS

29449 C8H20N 2 06 P22 32062 C9 H2 2N304PS

28669 C 11H 25N404 PS 32063 C 12H 20N304PS

29005 C1 3H 29NO2S 32064 C 16H 28N304PS

29006 C4H6 C13NS 32065 C1 1H1 5 N20 3PS

29237 C9H 21N2OPS 32067 C 27H 57N3042

29563 C10 H2 4N204S2 32379 C1 1H1 6 N203 S3

29654 C8H1 1N303S2 32558 C2 2H4 2 B2N2 045 2

29655 C6 H1 4N2 03S3 32564 C10 H2 3NS

29668 C1 1H2 7N403PS 33277 C24 H 48N2 02S2

29669 CH 22N304PS 33278 C1 0 H2 6N4 S2

29670 C1 7H21N304 S2 33583 C1 1 11 9NS25 1

29671 C1 9H2 7N304 S2 33584 C12 H2 1NS2S1.

29672 C1 1H2 4N4 04 S2 33585 C1 1 H2 1NS2Si

29673 C9 H NOS 33587 C1 4 H1 3N3 82

29691 C12 H1 7N03 S2 33711 C1 5H2 5NOS

29692 C1 3H19 NO4S2 33712 C H O25SN42

30089 C4 H8 CI3 NOS 33713 C2 4 H4 8 N22 2

30461 C H 22N2OS 33714 C2 8H4 4 N202 S2

820

WR No. Molecular Formula WR No. Molecular Formula

33715 C1 3H2 7NS 33897 C14H2 3NOS

33716 Cis H 31NOS 33944 C5H9N3S2

33717 C1 3 H2 1NOS 34140 C1 4 H2 9NS

33718 C3 0 H6 0N202 S2 34141 C1 5H2 9NS

33762 C1 2 H1 5N30 3 S2 34142 C1 4H2 1NOS

33764 C7 H1 0 N2 03 S3 34408 C1 lH2 4N2 S

33767 C8 H1 7 N3 05 S2 34409 C1 5 H3 2 N2 S

33768 C9 H23N 3 03 S2 34425 C1 2H28N2SSsi

33769 C6H1 7N2 03PS 34426 C14 H25NS2Si

33770 C8H1 8N2 S2 35112 C13H17N303S2

33771 C12 H21 NO3 S2 35997 C1 4H3 4N20 6P2 S2

33772 C9H1 7NO3 S2 35978 C3H1 0 NO3 PS

33773 C6H16N2S 35979 C 12H 22NO 3PS

33775 C10 H2 4N2SS1i 35980 C9 H23N 3S

33782 C1 6 H1 9N3S 35982 C7H14 N2 S

33783 C1 3H1 8FetO 3 PS 35983 C7H1 8N2 S

33785 C1 5H32N304 PS 35984 C9 H1 4N2 S2

33786 C1 5H20N304 PS 35985 Cs5H1 2N2OS

33787 C3 1H6 6N50 3PS2 35986 C7H1 8N2 03 S2

33788 C1 6H2 2N3 03PS2 35987 C1 2H20 N4S

33789 C1 2H17N04 S2 36159 C2 8H4 4N2 02 S2

33790 C31H6 5N5 03 S3 36160 C14H2 3NOS

33791 C1 3H1 7FeN 3 S2 36161 C11 H19N304S3

33895 C26 H4 0N202 S2 36162 C13H25NS

33896 C30 H4 8N20 2 S2 36163 C14 H2 7NS

821

WR No. Molecular Formula WR No. Molecular Formula

36164 C5'.llNOS 37720 C1 2H1 8N2 04 S2

36165 CisH3 4N4 08 S4 38485 C1 3H2 3NS2Si

36174 C6H1 4N4S4 38486 C9H2 3N03 SS3i

36246 C6Ho1 N2O5S2 38488 C14H18N20 4 S2

36247 C1 9H2 3N04 S2 38489 C1 5H2 3NOS

36248 C2 7H5 8N30 3PS2 38490 C1 4H2 1NOS

36249 C1 7H30N30 5PS 38491 C2 684 0 N20 2 S2

36951 C1 6H36N202S 2 38492 C1 4H2 7NS

36952 C2 6H52N2 S2 38493 C1 5H2 5NOS

36953 Co1 0H18N20 4 S3 38947 CIIH2 8N2 02 SSi

36954 C131H25NS 39045 C9 H1 3N30 3S2

36955 C16 H21CN 2 04 S2 39046 C9H1 4N20 3S3

36956 C 13H 21NOS 39047 C H 13CN 203S3

36957 C1 3H2 7NS 39066 C11H19NS 2Si

36958 CisH2 5NO4S2 39067 C 14H2 7 NS2 Si

36959 C2 6H52N2 S2 39068 C1 4H2 5 NS2 Si

36960 CisH2 5NOS 39742 C13H2 7 NS

36978 C1 1R2 6NO4PS 39743 C1 5H2 3NOS

37675 C14 H1 8N2 OS 39744 C1 6H2 5NOS

37678 C9H1 4N204 S2 39746 C8 H1 7NOS

37679 C9H1 4N204 S2 39747 C14H2 3N3OS

37696 C1oH1 9NS2St 39748 C1 4H3 2N2 0 2S2

37709 C4H7N3OS 39749 C18H31NO4 S2

37710 C3H8N2 S2 39750 C1 3H1 9 BrCINO4 S2

37719 C10H20N203S2 40333 C7 H 13N3S2

822

WR No. Molecular Formula WRNo. Molecular Formula

40334 C12H2 3NO3S2 42405 C6H14 N20 2$2

40335 C12 H24NO3PS1 42595 C1 gH32N202S 2

40336 C12 H18 N40 2S 42596 C1 9H3 2N20 2 S2

40337 C7H1 4N20 3S2 42597 C9 H2 2NO4PS

40338 C13 H20 N205 S2 42756 C4 H80 2S2

40339 C12 H1 4N2 05S2 42757 C7H1 9NO3S2Si

40340 C12 H1 5N2 05PS 42758 C13 H2 5NS2 Si

40341 C1H 16N205S2 42759 C1 2H2 3NS2 Si

40342 C1 3H1 7N2 05PS 42760 C16 H2 5NOS

40343 C1 4H1 8N205 S2 42761 C1 7H2 4N204 S2

40640 C17H29 NO4S2 42762 C2 4H3 6 Br2N402S2

40641 C1 3H20 N2OS 42763 C9H19 NOS

40642 C34 H46 N402S2 42764 C1 2H19 BrN20S

40643 C2 6 H4 0 N2 04 S2 42765 C1 3 H2 3 N3 0 4 S2

40644 C3 0 H4 8 N2 0 2 S2 42766 C1 3 H23N3OS

41040 C1 7HI6N402 S 43525 C9H1 oN2 S

41245 C 12H 23NS 43893 C 30H 48N202S

41261 CTH N1 S 43894 C1 8 H 240S7 142 1824ý2

41262 C8 H1 6 N2 S 43895 C13 H2 4 N2 S

41263 C9 H1 9 NO2 S 43896 C 141 23N3CS

41264 C1 0 H2 1 N02 S 43898 JP19 BgN2 0S

41265 C8H2 0NO6PS 2 43899 C_:8v 31N042

41266 C 1H 16N 2O 30 CVbqDN04s1126 1H6N 204S2 43900 4i qB' 2bS

41788 C3H6 N2 S 43901 -C H N0s

42394 C7H N3S 44152 CIH6N2OS7 19 3 3 C1 3H1 6 28

823

WR No. Molecular Formula WR No. Molecular Formula

44153 C 13H6 N 2Os 50489 CH 24CIN05S

44154 C1 3H16 N2 04S2 50908 C6 H13NOS

44923 C6 H1 7N203 PS 50909 C6H1 6N6 S4

46358 C7H1 6N303 PS 51519 C8H2 3NSSI 2

46359 C7 H1 5N204 PS 51520 C8 H2 1NO3S2 Si

46360 C1 9H2 7N40 3PS 51545 C9H1 5 NO2 S2

46361 C24H40NO5PS 51691 C6H1 7NO3 S2 Si

48677 C6H9NO2 S2 51983 C1 2H21 NS

48678 C8H1 5N03S2 51984 C11H26 N2 06 S4

48679 C H N3S 51986 C H NO2S,13 25 3 10 17 22&

48680 C24H44N2S2 51988 C H 17NO2S2

48681 C13H2 3N3S 51989 C14 H19N205 PS

48682 C1 2 H1 8N4 05S2 52114 C1 1H26 NO5PS

48683 C6H1 2N2G3 S2 53374 C H 21NO3 S 3Si

48684 C6H1 2N402 S2 53376 C H 21NS 2Si

48948 C17H16N4 0s 2 53377 C7H 7NO3 S 2Si

48950 C5H10 N2OS 53378 C1 2H2 1NS 2 Si

49563 C 12H 21N204PS 53470 C H O24N2s

50480 C1 2H19 BrN 204 S2 54202 C1 0H1 5 BrN2OS

50481 C8H1 6 ClNS 54203 C H 15BrN2 0 4S2

50483 C19H35N308S4 54204 C 15 20N204S2

50485 C1 2H21NO2S 54205 C 13H27 NO 3S2

50486 C1 3H24 CINO4 S 54206 C1 3H2 3N3 04$2

50487 C14 H2 6CINO4 S 54207 C14H23NO4S2

50488 C1 5H2 2 C1NO5 S 54208 C16 H3 3NO4 S2

824

WR No. Molecular Formula WA Nc. Molecular Formula

54209 C1 6 H27NO4 S2 61135 C1 5H2 3NOS

54550 C11 H18N303PS 611C6 C9H18N2S2

54551 C1 2H1 7NOS 61137 C12H23 NO2S

54554 C1 3 H2 1N03 S2 61138 C1 5H2 0 N2 OS

54556 C7H 14N202S 61139 12H 22N 203

54558 C11H15NO4 S2 62069 C5H12N2S

54818 CH lNO,' 62459 C2 0 H NS 45 11 2026 44

57669 Co 0 62460 C1 4 H2 7 N3 S2

57857 C2 2H4 6 NIO2S2 62461 C 13H 26N2S

59417 CsH2NOsPS 62940 C H N20SC8H20N055 15 20252

60185 C1 0 h8F 1 5NO3S2 62941 C1 1H2 8N206P2S 26u187 c6hF7N0IS2 62942 C H 26N206S4

60188 CSH813NO3S2 62943 C 12H 28N206P2S2

6023? c1 2H 18U!204S2 62944 c1 2H2 6N2 S2

60238 C11H 1 6 N20 3 S2 62945 C7H1 9N2 03 PS

60239 C9H1 2N2 S 62946 C5H1 0 N2 0 3 S2

61126 C 17.211304PS 62947 CH 14N2S

61127 cIOHI3NOS 63083 c12 H1 8 N 2S2

61128 C1 1H1 5NOS 67627 C1 2 H18N402S

6112? C1 1 H16 N2 IS 67634 C1 3H20 N40 2S

61130 C1 2H18 N2 LS 67638 H11N02S

61131 C4H9NS 67657 C9H 1 7NO3S 2

61132 C6H 13NOS 67698 C4H 12N303PS

61133 C4 H 27NS 67803 C8H 1N3S

61134 C6 H 20N 2OS 67808 c9H 3N3S

825

WR No. Mlecular Formula WR No. Molecular Formula

67833 C1 1R14 N40 3S2 74128 C1 8H3 9N2 03PS

68815 C1 4H29 NO3S2 74129 C1 2H 1 5N2 05PS

69062 C1 2 H1 /BrN 3OS 74130 C1 5H2 3 FeNIO3PS

69884 C 10H 22NO3P;3 74131 C 17H 27FeN203PS

69885 C1 0 {2 2NO3PS 3 74132 C1 9 H2 5NOS

69886 C12 H26 NO3PS 3 74169 C1 6H2 8N03PS

70035 C1 1 H26 N3 04PS 74170 C9H1 7NS

70036 C8 H1 2AsN0 2S 74171 C9H1 8NO3PS

70037 C10 2 3N204PS 74172 C"15 N203PS

70038 C 16H 27NO3 S2 74173 C15 H2 1N2OPS

70039 C1 1H2 5N2 03PS 74174 C1 7H26N30 5PS

70040 C H 27N203PS 74175 C H H25N35S2

71460 C12 H19N 3S 74176 C1 2 H2 6N2 06 S4

71462 C1 2 1 8 BrN0 3 S2 74177 C4 H11N3OS

71463 C 11H1N304S2 74178 C1 1H2 6N304PS

71466 C15H25N0482 74326 C9H 1NS

71471 C1 4H2 9 NO3 S2 75232 CH 24NO 3PS

71475 C 22H 36N 602S 75233 C4 H 8N406S4

73853 C8 H16 NO4 PS 75234 C15 H26 N20 4S2

74054 C1 5 H24 N2 0S 75235 C1 8H36 NO3PS

74056 C14H2 3NOS 75236 C i 1 9N30 6S2

74058 C 13H 20N 2OS 75237 C1 4H2 3N04 S2

74062 C1 2H2 1N2 03PS 75238 C1 4 H2 3N04 S2

74126 C1 4H2 9N2 03PS 75611 C6H 8N 2S

74127 C1 4H3 1N2 03PS 75612 C16H 8N 2S

826

WR No. Molecular Formula WR No. Molecular Formula

75613 C4H10 N2S 76970 C8Hl 5N2 OsPS

75614 C8H1 0N2 S 76971 C9H1 6 N2 05 S2

75615 C14H15IN2s 76972 C9 H1 7N205 PS

757'9 C1 0 H1 0 BrN3OS 77548 C6H 15NO2S3

76062 C1 1 H1 8 N2 S2 77913 C3 H1 0 NO4 PS

76063 C4 H 8F 3NOS 79336 C1 1 H1 5 N4 03 PS

76733 C5H11NS 79337 C H 14N4S

76734 C10 H25NOSSi 80316 C 13H 21N23

76735 C1 4 H2 7N03S3Si 80393 C1 2H2 7N20 3PS

76736 C1 2H2 3NO3 S331. 80394 C1 4 3 1N20 3PS

76737 C7H1 9 NSSI 80395 C6H14N404S2

76738 C8 H2 2N2SSi 80396 C1 2H1 8N404S2

76739 C9 H2 1NSSi 80397 C1 7H2 3N304S2

76740 C7H19 NOSSI 80405 C1 6H3 3N20 3PS

76741 C8H21NS 2 Si 80406 C6 H 35N203PS

76742 C1oH25 NO4 S2 Si 80407 C2 0H4 3 N20 3PS

76840 C9H1 oN20 3S2 80408 C1 9H3 4 FeN20 3PS

76841 C4H1 oN2 S 80409 C1 1 H2 7N40 3 PS

76842 C2 H6 N2 S 80410 C9 H1 7N04 S2

76843 C8 H1 7NO3 S3 80411 C8H 11 AsCCNO2S

76844 C8H17N04S3 80685 C4H12N2S2

76966 C10H19N3S 80783 C1 2H1 6N40 3S2

76967 C12H26N2S2 80855 C7I7 N203PS

76968 C12H28N206P2S2 80856 C1 3H16N4OS

76969 C8H14N2O5S2 80857 C 14H 19N205PS

827

-% - :TW

WR No. Molecular Formula W -No. Molecular Formila

80858 C8B1 4N2028 2 81893 C11H15No582

80859 C10 H1 5 C1N2 04 S2 82409 C 1 0 12N20 2S

80860 C60 12 C1NS 82422 C1 2 R19 ClN2 04S2

80862 C10H1 21 2OS 82969 C4 H1 2N2 S2Zn

80863 C1 0 812H2 S2 84133 C 101N205S2

80864 C3 HeN2 0S 84134 C1OH1 9N205PS

80865 C12H 20 N205 52 84135 C1 5H20 N4 02S

80866 C20 H2 8Br2N402S 2 84136 C1 7 H34N202 S2

81009 C4U8N202S2 84137 C8H1 5NO3S2

81579 C10 H1 5IN 2 S 84138 H4NO2 PS

81580 C1 0H1 4N2S 85561 CoH11 NO2 S

81581 C1 4H1 2N20S 85562 C13 H19 C1N20S

81582 C1 6H2 4N20S 85563 C 12H 19CIN 2Os

81583 C7H BrN3S 85564 C a N3S7 18 3 15 .2.1 3 2

81855 C61 1 5N4 03PS2 85565 C 31? 2 2"20 4S2

81856 C1 1H2 3N203 PS 85566 C2 4H36Ci 2N40 2S2

81857 C1 8H 3 8N203S2 85567 C1 5H22N20 2S

81858 C8HAsN 204S 86101 C4H 12N2NIS2

81859 C 10HiAsN204S 87331 C 15H 23NO3 S3

81860 C9H1 9 NOS 2 87332 C8 H1 7NO6 S3

81861 C3H1oN2 S 88294 cH 10N203 S2

81862 C1 0H14 N2S 88299 C 12 H 19N3S3

81864 C11H14 N20 2S 88300 C10 H1 4N2S

81866 C9 H1 8N2 S 88301 C8H1 8N2OS

81867 C10 H2 2N2S 88302 C5H1 4N4 S

828

WR No. Molecular Formula WR No. Molecular Formula

88304 C9H2 0N2OS 90243 C6H1 4N4 S2 Se2

88305 C5 H1 0N2S 90704 C1 3H2 3NO04 S2 S1

88307 C9 H1 6N203 S 90707 C20H5 0 N4 S4 S12

88309 C8H1 0N4 05 S2 91480 C4 H1 3 AsN202 S2

88310 C8H1 8N40 6 S4 91482 C 10H 24NO3PS

88311 C7H16NIS 91483 C10H24 NO2PS 2

88885 C6H1 3NS 91484 C8H17NOS 2

88894 CSH21N203 PS2 91485 C9 H1 6N2 02S

88895 C1 2H1 7N4 03 PS 2 91486 C14 H18 N2 02S

88897 C8H1 3AsN2 02 S 91487 C20 H2 1FeNOS

88898 CBollASN2 5 S 91488 C1 7H2 2N2 S2

88899 C7H1 6N2 S2 91489 C10 H1 5N3 06S2

90185 C1 4H2 7NS2Si 91490 C1 1H1 8N2 S3

90187 C1 4H1 9N30 3Si 91491 C1 3H2 2N2 OS

90188 C1 4H1 7N3OSSi 91492 C1 1H2 0N2 S3

90200 C1 4H 1 N20 5S2 91493 C1 0H1 5N3 06 S2

90201 C9H22N206S4 91494 C 13H 21BrN204$2

90202 C10H24N206S4 91495 C1 3H2 1BrN20S

90203 C1oH22N206S4 91496 C4 H 21ErN2OS

90204 C1 0H24 N20 6P2S2 91497 C H 16N4 S2

90205 C1lH18N4S2 91499 C 26H 40Br2N402S2

90206 C6 H1 3N02 S 91635 c 12H25 NO3 S2

90240 C26H54N4S4 91824 C6 H1 5 IN2 S

90241 C8H1 8N4 S4 92434 C8H1 0FN30 3S2

90242 C6H16N6S4 92437 C8H9N3S2

829

WR No. Molecular Formula VR No. Molecular Formula

92438 C08 11 N3 03 S2 94530 C5 H1 2N2 02 S

92439 C6R1 3N3 05 S2 94531 C1 7H2 9BrN20 4 S2

92440 C9H1 3N3 04 S2 94532 C18 H29 BrN2OS

92441 CHI N06S 94533 -4 .,NOS4 10 2 64 . '4 2

92485 C9 H9NO2 S 94534 ..N204S2

92967 C7 H15N 5S3 94535..,s

92968 C2 H 1NO3S 94536 C 179 BrN2OS

92969 C14H3 2N2 06 S4 94537 C3 ' 5 6 Br2N4 02S2

92970 C12H2 8N 2 06 S4 94538 C1 4112 2N2OS

92971 C 11H 26N206S4 94539 C14 30N2S 2

92972 C18H1 9 N30S 94540 C9R20 N2OS

92973 C1 2H2 2N203 S2 94541 C1 3H28N20S

92974 C5H11NS 94542 CI3 H1 9 IN2 OS

92979 C16 H3 0N3 03 PS 94543 C16 H2 5 BrN2 OS

92980 C18 H2 4NPS 2 94789 C7H1 5 NOS 2

92982 C 10H 3NOS 94790 C 12H 17NOS2

92983 C13 H1 9NOS 2 94791 C1 3H24N20S

92984 C 12H 16N202S 94792 C1 3H1 7N03 S

92985 C18 H 26N2OS 94793 C1 8H28 N40 2S

92986 C1 3H1 4N20 3S 94794 C1 8H18N2OS

93238 C9H1 2N20S 94795 C4H8N2 03 S3

94140 C1 3H2 2N20 3S2 95565 C1 1H1 1NO3S

94292 C10 H1 8 N20 3S2 95566 C10H10 N20S

94293 C1 2H22 N20 3 S2 95567 C10 81 1N0S

94529 C 14H 21BrN2OS 95568 CH 10C3NO 2S

830

WR No. Mtolecular Formula WR No. Molecular Formula

95569 C1 6H1 5 NO2 S 98131 C9 H18N20S

95570 C5 H7F66NOS 99575 C1 2H1 9 IN2 04S2

95571 C1 1H22 N2 04S2 99576 C10 R1 3 BrN20S

98060 C9 H1 6N2 03S2 99578 C6H140 2S2

98073 C 10 1 7N3043 2 99579 C1 3B2 2N20S

98074 C1 3R1 60 200S2 99580 C1 6H33 82

98075 C1 4H1 8N205S2 99581 C12HisBr2N204S2

9876 c813304 s2 99582 C12 19BrN204S2

98077 C1 2H2 2N408 S4 99583 C13 H18 Br2N20S

98078 C8H13 oN3 S 99584 C1 3H,19 rN oS

98079 C1 4 H18 N20 2S 99585 C1 8 H3 7NS2

98080 Co1 0 16 N204 S2 99586 C9H13BrN2OS

98081 C10 " 1 7N3 04S2 99587 C1 2H1 9 1N2OS

98082 C15 H20 N204 S2 99588 C1 2H1 8 Br2N2OS

98101 C1 51R2 7NO3 S2Si 99589 C2 4H34 Br4N40 2S2

98109 C1 8R3 0N40S 99590 C9 H1 3N2 04S2

98110 C1 8H28N202 S 99597 C1 6H36 N2 06 S4

98111 C1 9H26N2OS 99598 C15H34 N2 06 S4

98112 C1 8H30N20 2S 99599 C1 2H30 N4 S2

98113 C10 H1 5N30S 99600 C9 H14N204 S2

98114 C1 5H1 7N30S 99601 C10H1 8N205 S2

98115 C 13H 16N2OS 99602 C 12H 20N2S2

98116 C1 4H 1 7F6 N3 0S 99603 C7H1.5NO2S2

98117 C7 H10 F6N2OS 99604 C7H16 NO5PS

98120 C8H1 8N4 S4 100555 C5 H1 2N20S

831

WRI No. Molecular Formula WR No. Molecular Formula

101822 C8 12 1NOSSi 104702 C24H3 6Br2 N40 2S2

102230 C1 7H2 0N2S 104703 C1 2B1 7BrN2OS

102231 C1 40 2 6N2 S 104704 C9H1 3 C1)N204S2

102232 C9 H1 7N02 S 104705 C1 5H1 8N2OS

102233 C8H10 06 S4 104706 C1 6H2 2N204 S2

102262 C6 H1 3N203 PS 104707 C7H10 02S

102263 C9H1 9NO2 S 104708 C7 1202S

102264 C7H1 2N20S 104709 C8 H1 404 S2

102265 C 2H, 4N2 0S 104710 C12H2 202 S2

102266 C1 1H1 5NOS 2 104722 C1 4H2 4N205S2

102267 C1 6H2 6N20 2S 104723 C1 3H2 2N205 2

102268 C16H24N20S 104724 C H120N20 5S2

102269 C2 0H2 7N30S 104725 C13H30 N2 06 S4

102270 C9H1 2N20 3S2 104731 C14H3 4N2 06P2S2

102547 C1 2H1 8N2S 104733 C1 1H2 8N206P2 S2

103582 C2 H6N2OS 105131 C1 2H1 2N203S

104302 C5H1 2N2 03S2 105132 CaH18 N2OS

104694 C7 H 14N2 105436 C6H1 1N02S

104695 C1 1H1 7BrN20 4S2 105442 C1 1H1 3NO2S2

104696 C1 2H1 9N306S2 106155 C11H1 7BrN2OS

104697 C1 4H2 2BrC1N20S 106156 C14H18 N20402

104698 C1 8H2 4 Br2N4 02 S2 106157 C18H26 N204 S2

104699 C1 2H1 9 BrN2 OS 106158 C19 H26N20S

104700 C14 H1 8 N204 S2 106159 C1 3H2 1CIN4 OS

104701 C1 0H1 3 C1I 2S 106160 C15H1 8N20s

832

WR No. Molecular Formula WR No. Molecular Formula

106161 C 15H 18N 2OS 108532 c 1 2 H2 9 N 2 PS

106162 C1 3 H2 1 C1N2 04 S2 108537 C1 3 H1 8 N4 02 S

106163 C1 7 H2 2 N2 OS 108538 C1 4 H32NO3PS

106164 C2 6 H 40C2N402S2 108539 C 16H 20NPS3

106165 C 13H 21CN 2OS 108540 C8 H2 0 NO3 PS

108250 C2 H7 N2 03 PS 108541 C9 H2 1 N3 S2

108417 C1 3 H2 5 NO3 S 3 S1 108542 CTH 1 6 N2 0S

108424 C9 H2 0 N4 06 S4 108543 C8 H1 7 N02 S

108501 C1 7 H2 2 N2 OS 108544 C1 2 H20N2 04S 2

108502 C1 5 H1 9 C1N2 04 S2 108571 C1 4 H3 1 NO2 S 3

108503 C1 4 H2 1 C1N2OS 109342 C1 3 H2 2 N2 S

108504 C1 1 H1 7 CIN2 04 S2 109343 C9 H H 9N30S

108505 C12H 1 7 CN 2 OS 111477 C4 H8 0 2 S 2

108506 C1 H 28N42 111478 C 1224 N2044

108507 C16 H38N 2 06 P2 S2 111479 C2 2 H3 4 N2 0 3 S2

108508 C1 5 H3 6 N2 06 P2 S2 111485 C1 1 H1 7 CIN2 OS

108509 C1 3 H3 2 N2 06 P2 S2 111486 C1 6 H2 1 CIN2 04 S 2

108510 C1 0 H2 6 N2 06 P2 S2 111487 C1 6 H1 9 CIN2 OS

108511 C8 H2 2 N2 06 P 2 S2 111488 C1 7 H2 1 C1N 2 OS

108512 C 14H 25N2OPS 111489 C 16H 28N2042

108513 C1 3 H2 3 N205 PS 111490 C1 61H2 2 N2 05S2

108514 C1 2 H2 1 N2 05 PS 111491 C1 6 H2 2 N2 04 S2

108515 C7 H1 5 NS2 111492 C1 7 H2 3 C1N 2 04 S 2

108530 C1 3 H2 4 N303PS 111499 c 20 H20 NPS 2

108531 C9 H2 1 N2 0 3 PS 111500 C1 6 H2 0 NPS 2

833

R, No. oleculor Formula WR No. Molecular Formula

111501 C1 2 H2 0 NO2 PS 2 117900 C1 2 H1 9 BrN2 04 S2

111502 C1 2 H2 0 N03 PS 117909 C1 2 H2 6 NO3PS

111503 CloH1 6N02PS2 117914 C1 4 H2 4 NO4 PS

111504 C6H1 6 N02PS2 117917 C1 5H2 6NO4PS

111505 C5H1 3 N3S2 117930 C16 H1 9 C1N2OS

111506 C4 HIIN3 S2 117931 C1 3H19 N304 S2

113191 C9H1 6N203 S2 117932 C1 4Hl 8N204 S2

113260 C1 0H2 5NOSSi 117933 C1 3H2 0N20S

114388 C1 1 H1 6N20 3S2 117934 C1 7H2 8N20S

114389 C8H1 7N3S2 117935 C11 H1 6 N20S

114390 C1 1H1 6NO3PS 2 120767 C1 3 H21 N04 S2

114391 C3H1 1 N20 3PS 120768 C1 7H23 C1N2 04S2

114392 C8 H2 1 N20 3PS 120769 C1 5H1 9 C1N2 04S2

114393 C 10H 19N 20 5PS 121223 C2 0H24 N402 S

114394 C1 5H2 0N20 5S2 121224 C H 21N20 5PS2

114395 C14H18N2O5S3 121225 C4 H 9N205PS2

114396 C1 5 H2 0 N2 0 5 S3 121226 C1 6 H 2 2 N2 05 S 2

114397 C H 24N4OS 121227 C2 2H28 N2 S4

116728 C5H11 N3S2 121228 C1 2H1 7 N3S2

116731 C717N3S2 121229 C H 15NS2

117247 C3 H9N3S2 121230 C11 H1 5 NO3S3

117403 C9HI2N20 3S3 121231 C1 2H21NO3 S2

117404 C3H8N20s 121334 C8 H 8S2

11.7405 C1 OH2 203 S2 121448 C1 5 H2 1NO3S2Si

117883 C1 8H2 3C1N 20S 121449 C1 1H1 202 S2

834

WR No. Molecular Formula WR No. Molecular Formula

121450 C9HI 7N3S 123930 C8H6 C12 0S2

121451 C7HI4N404S2 123932 C3 H 6OS2

121769 C1 2H2 1NO4 S2 Si 123934 C1 1H1 4OS2

127157 C H N2OS 123935 CgH1 0OS29 18 L2 1

122158 C8H1 6N20 2 S 123947 C4H8 02 S2

122159 C9H19NS 123948 C1 8H2 4N202S

122160 C1 3H2 5NO3 S3 S1 123949 C1 9H2 6N20S

122167 C1 1H1 3N3OS2 123950 C1 5 H24N20S

122951 C2 5H2 3 NOSSI 123951 C1 7H2 2N20S

122952 C1 2H2 1NO3 S2Si 123952 C1 8H2 3CIN20S

122957 C1 4H2 1 NOS 123953 C1 8H2 6N204 S2

122958 C1 6H2 0 N2 02 S 124940 C1 5H2 6N204 S2

122959 C1 7H2 4 N205 S2 124950 C1 3H20 Br2 N2 04S2

122960 C15 H20 N205 S2 124951 C1 9H2 8N204 S2

122961 C1 0H1 5C1N20S 124952 C2 7H2 6N20 2$S1.

122962 C1 1H1 5 C1N2OS 125046 C4 H1 2N2 S3

122963 C1OH15CIN204S2 125047 C8H17NO2S

122964 C2 0H2 8 C12 N4 02 S2 125049 C21 H4 4 N304 P$

122965 C9H1 60 2S 125050 C1 1 H2 7N203 PS

122966 C1 4H2 8N6 04 S2 125051 C8H1 8 NO5 PS122967 C14H19N50 125052 CH 22N303PS

122968 C1 5 H2 0 N205S 2 125053 C11H26N2 03 S2122969 C4H802S2 125150 C H 13N2S

122970 C16H22N204S2 125439 C0 H21 N03S2

123086 C 9H7NO2S2 125677 C 16H 29NO3SSi

123087 C8H1 6C1NS 2

835

WR No. Molecular Formula WR No. Molecular Formula

125678 C3 4 H5 9 NO3 S2 S12 132190 CTH 1 6 N2 OS

125688 C9H2 4N206P2S2 132191 C5H8 CI3NS

125689 CgH2 2N206 S4 132192 C H BrN2S2

125690 C1 3 H1 9N20 6PS 2 132193 C14 H 22N2 Os2

125691 C1 3H1 8N20 6 S3 132194 C1 4 H21 ClN2S2

125692 C1 2 H17 N20 6 PS2 132195 C11 H1 5 C1N2S2

125693 C1 2 H1 6N2 06 S3 132196 C18 H2 1 F3N20S

125694 C11 H140 2 06S3 132197 C14 H2 11N2 OS

125695 C7 1H5 N302 S2 132198 C5H7N20 2PS

125696 C12 H2 2NO3 PS 132199 C1 7H2 1 F3N2 04 S2

125697 C1 2H2 1NS 132723 C9H10C1N 3S2

126158 C7 H1 9N203 PS 132725 C3H8 OS2

126452 C1 H24 N2S2 132726 C20H40N2s4

126453 C3H1 0 NO2 PS 132727 C1 2H2 5NS2

126454 C14 H2 0 Br2 N2OS 132806 H3NO3S 2

126455 C1 3H1 9 C1N2S2 132919 C1 21H18 F3N 0 3S2si

126456 C 17H 24N 20 4S2 132920 C1 6H31 No3S3 Si

126457 C18 H2 4N2 s 2 132921 C14 H2 7 N03 S3 Si

127014 C12H 17 N5 04 S2 132922 C1 1H1 8 BrNO3S2Si

127015 C H 7N 3OS 133564 C6)1 4 NOs5PS 2

127016 CH6NO2 PS 133565 C6H1 3N05S3

127017 C4 H1 2 NO2 PS 133566 C1 5H3 2NO3PS

128712 C8H1 7 N03S2 133567 C1 4H3 0N03PS

131155 C3 H 25NO 3S 3Si 133568 C1 5 H31 NO3S2

143189 C1 2H2 8 N2S2 133569 C1 4 H2 9N03 S2

836

WR No. Molecular Formula WR No. Molecular Formula

133570 C3 HIoN2 S 138411 C1 6 H2 5 N02 S

133635 C1 1 H1 8 ClNO3 S2 Si 138412 C1 2 H1 8 C12 N2 04 S2

134154 C7 H1 5 NO2 S 4 138413 C1 3 H1 8 C12 N20S

134783 C1 4 H2 9 NS2 138414 C7H15NOS

134784 C1 5 H1 7 F3 N2 04 S2 138415 C1 7 H3 5 NO4 S2

134786 C1 2 H1 7 N5 0 4 S2 138416 C6 HIoN2 S

134787 C1 3 HI 9 1N2 S2 138417 C3 H 18Cl2NS2

134788 C1 9 H2 6 N2 S2 138418 C1 8 H3 5 NOS

134790 C1 2 H2 3 NO3 S3 138419 C1 4 H2 7 NOS

136178 C1 6H1 7 F3 N2 S 138677 C1 7 H2 7 N2 03 PSSi

136179 C1 4 H2 9 NS2 138736 c1 5 H2 7 N2 04 PS

1361.80 C1 6 H2 6 N2 OS 138745 C1 2 H2 2 NO4 PSSi

136181 C1 6 H2 8 N2 04 S2 138746 C1 2 H2 2 NO3 PSSi

136182 C 7 H2 8 N2 OS 138747 C1 8 H2 4 N2 04 S4

136216 C1 5 H3 1 NS 138766 C1 8 H2 3 ClN 2 S2

136217 CIOH2 5 N3 S2 138768 CI1 H1 4 C12 N2 S2

136218 C1 0 H1 5 N04 S2 138769 C1 4 H2 0 CI 2 N2 S2

136219 C1 oH1 6 NO4 PS 138770 C2 3 H3 5 NOS

136220 C1 4 Hl 8 N2 05 S2 138775 C! 5 H2 2 NO3 PSSI

136864 CloH1 8 NS3 139241 C2 4 H5 2 N2 S4

136905 C1 4 H2 7 N2 04 PSSi 139242 C2 4 H5 2 N2 s 3

137263 C8 H1 9 NO3S 2 139243 C1 2 H2 8 N2 S3

137601 C9 H1 6 N2 02 S3 139244 C 2H 30N 8S3082

137602 C1 6 H2 4 N2 S2 139245 C1 oH 2 2 N4 0 2 s 2

138410 C1 3 H1 8 ClNOS 139246 C6 HI 4 02 S2

837

WR No. Molecalar Formula WR No. Molecular Formula

139249 C6 H1 8 SSi 2 145378 C1 5 H2 6 N2 04 S2

142069 C1 0 H1 1 NO4 S 2 145720 C1 2 H1 8 N2 0 2 S

142070 C1 3 H1 0 02 S2 145722 C1 4 H20N203S

142071 C1 4 H1 7 NO5 S2 145723 C4H 23BrN2 0 4S2

142073 C1 3 H1 8 N2 03 S2 145724 CIsH2 3 1N2 0S

142074 C1 1 H1 3 N3 05 S2 145725 C6 HI 2 N2 S2

142075 C1 4 H2 5 NS 145727 C8 H18 N2 04 S2

142076 C14 H2 6 NO3Ps 146020 C1 2 H1 5 N04 S2

142077 C1 4 H2 5 NO3S2 146073 C6 H1 6 N2 S 2

142078 C1 3 H2 3NS 146074 C4 H9 NOS 2

142079 C1 3 H2 4 NO3 PS 146075 C9 HIoN2 S

142080 C1 3 H2 3 NO3 S2 146076 C6 H1 1 N3 0S

142081 C8 H1 2 N4 S 146092 C1 1 H1 6 N2 04 S2

142489 C6 H1 7 N2 0 4 PS 146098 C17 H22 N2 0 2 S

142824 C9 H1 7 N2 03 PS 2 146099 C1 7 H3 3 NOS

143994 C6 H 31NOS 146104 C1 4 H2 7 NS2

143995 C2 2 H3 5 NO4 S2 146105 C1 4 H2 3 IN2 04 S2

143996 C1 2 H2 0 C1N 2 04 PS 146106 C7 H1 2 N2 S2

144974 CloH1 3 NOS 146107 C4 H1 1 N3 S2

144975 C1 5 H2 3 BrN2 OS 146108 C4 H1 2 N2 S4

144976 C1 5 H2 3 CIN2 OS 146109 C6 H1 6 N2 S3

144981 C1 2 H1 8 N2 05 S2 146110 C7 H7 NOS

145038 C9 HI 0 02 S2 147007 C11H13 N 30S

145039 C1 2 H1 6 N2 04 S4 147953 C4 H1 0 N2 04 S 2

145040 C1 4 H2 4 N2 04 S2 147954 C11 H 5 1N2 0S

838

WR No. N;lecular Formula WR No. Molecular Formula

147955 C2 6 H52 N2 S2 149528 C1 8 H2 4 N2 0 6 S2

147956 C H- 2 N2 04 S2 149750 C1 5 H2 6 N2 04 S2

148652 C3 HIIN5 03 S2 149846 C8 H2 1 N2 03 PS

148655 C1 5 H1 9 N2 07 PS 149847 C14 H2 4 N04PS

148656 C5H1N207S 149848 coH2N306P2S

148657 C1 4 H1 8 N2 0 6 S2 149849 C7 A 9 N2 04 PS

148658 C16 H2 3 N2 O5 PS 149960 C4 H4 N6 S4

148659 C1 6 H2 3 N2 05 PS 150066 C8 H1 4 N2 05S

148660 C1 6 H2 2N0S 2 150Co9 C1 7 H2 2 N3 03 PS

14866] C1 5 H2 1 N2 0 5 PS 150070 C2 3 H3 4 N3 03 Ps

148662 C1 5 H2 0 N2 05 S2 150072 C1 4 H3 3 lO 3 SSi

148663 C1 1 H2 1 N2 05 PS 15073 C1 6 H3 7 NO3 SSi

148664 C1 0H1 5NOS 150075 CI8 H4 1 NO3 SSi

148665 C2 9 H5 3 N03 S2 150076 C6 H1 4 N20S

148666 C1 4 H2 5 NO3S 2 150077 C1 2 H2 6 N20S

148667 C2 6 H4 4 N2 S2 150078 C9 H1 2 N2 OS

148743 C1 2 H1 7IN2 0S 150079 CHilN0 2 S2

148744 C6 HI 2N2 04 S2 150080 C4 H9 NO2 S 2

148746 C9 H1 3N3 0 3 S2 150081 C6 Hl 3 N02 S2

148747 C6 H1 4 N2 0 5 S2 150082 C9 H1 1 NCS 2

148768 C14 H2 3 NO4 $2 150084 CisH2 0 N2 02 S3

149023 C8 H2 1 N2 0 3 PS 150243 C1 IH1 4 N2 02 S

149024 C1 4 H3 4 N4 S2 150244 CllH1 6 N2 0 2S

149346 c 18 H2 4 N2 06 S2 150245 C1oH14N20S

149526 Cl 0 H2 0 N2 04 S2 150248 C7 HI 6 N2 0S

839

Vk No. Molecular Formula WR No. Molecular Formula

150249 C1 0 H1 4 N2 0S 151355 C1 5 H2 4 C1N3 0S

150632 C1 21 2 4 N2 03 S2 151356 C1 3 H2 8 N2 S

150633 C1 0 H2 0 N2 03 S3 151358 C1 5 H2 8 N2 04 S2

150634 CII I CN2 S 152105 C8 H1 2C12S

150637 C1 0h2 0N20 3S2 152910 C10 H2 3NO4 S2

150639 C1 8H30N2OS 152911 C1 1H2 5NO4S2

150640 C1 3H2 2N20 4S2 152912 C1 3H2 9 NO4 S2

150641 C14.22N 2 2 152913 C H 24NO 4PS

150724 C6H1 6 N2 04 S4 152914 C1 3H30 NO4PS

150728 C1 6H3 1N06S2 152915 C1 1 H2 6NO4PS

151320 C1 0H2 0 N20 2S2 152916 C1 2H2 7N04S2

151321 C1 5H2 8NO3PS 152917 C1 2H28 NO4 PS

151322 C1 4H2 3NOS 152918 C8 H19 NO4 S2

151323 C1 5H2 7NO3S2 152919 C9 H2 1NO4S2

151324 C6H1 7 N20 3PS 152922 CIH 2 3NS2

151325 C5H15 N2 04 PS 152923 C5H1 1 N05s 2

151326 C7H18 N2S 152924 C1 2H2 5 NS2

151327 C7H1 9N2 03PS 152925 C1 4H211N2S2

151328 C2 8H3 0N204P2S 2 153733 C5 H1 002 S

151329 C1 8 H2 2 N02 PS 154256 C6 R1 3 NO2S

151330 C1 6 H3 2N2S 154621 C8 H9 NO2S2

151331 C20 H38N 4 S2 154711 C5H 120G

151332 CI6H2 4 BrC1N2 0S 154975 C1 oH2 1NS2

151333 '. 15H24 BrN3OS 154976 CIoH21 NS2

151334 C2 3 H3 1N30S 154977 C1 2 H25NS2

840

WR No. Molecular Formula WR No. Molecular Formula

154978 C1 3H2 7NS2 156903 C1 8 H2 4 N2 04 S4

154979 C1 5H3 1NS2 156916 C8 H6 04 S2

154980 C1 7H3 5NS2 156917 C1 5 H2 8 N2 04 S2

155419 C2 6H4 2N4 S2 157066 C8 H1 7 NO2 S

156714 C H 23NS 2 157067 C9 H1 9 N02 S

156715 C1 2H2 5NS2 157069 C8 H1 6 0 2S2

156716 C1 3H2 7NS2 157070 CgHllNOS 3

156717 C1 3H1 8 Br 2N2 S2 157071 C1 3H1 9 NOS 3

156718 C14 H2 9NS2 157072 C1 4 H2 9NS2

156720 C1 8H3 7NS2 157073 C1 4 H2 9NS2

156772 C6H14NO2PS 157075 C1 4 H24 N2 0 3 S2

156773 C16H27 NO5S2 157076 C1 5H3 1NS2

156783 C1 6H28 NO5 PS 157077 C1 5 H2 6N2 0 3 S2

156784 C15 H2 7NS 157078 C1 5H2 6 N2 S

156786 C4 H80 2 S2 157079 C1 6 H3 3NS2

156787 C6H1 7N203PS 157086 C H 31NOS22

156788 C6H1 6N2 S 157087 C1 4 H2 9NO2 S2

156789 C8 H2 0N2 S 157088 C1 4 H2 9NO2S2

156790 C8H1 204 S2 157091 C OH26 N 4S3

156791 C8 H1 20 5 S2 157092 C9 H1 8 OS3

156792 C9 H2 2N2 S 157094 C9 H20 N2OS

156793 C1 0H1 9N20 3PS2 157095 C H 9NOS2

156794 C1 1H2 0 N3PS 157097 C8H 1NO2S2

156796 C 14H 25NOS 157099 C8 H1 7 NO2S

156803 C10 H1 1NO4S 2 157101 C7 H. 6 N2 0 2 S2

841

WR No. Molecular Formula WR No. Molecular Formula

157103 C6 H1 6 N6 S6 158492 C8 H1 6 N2 0 3 S2

157104 C6H1 4N202S2 158493 C1 3H3 oNO3PS 2

157105 C6H1 3N02S2 158494 C 14H 29NOS

157106 C6 H 3NOS 2 158495 C H H31N2

157107 C6H1 3NO2S 158498 C1 8 H2 9C1N 2 S2

157108 C5H NO2S 158502 C H N4S5 11 2 2 30 504 2

157112 C4 H8 03S2 158924 C11 H22 N4 02 53

157113 C2H7NO3 S3 158925 CIIH1 5NOS 3

157297 C1 6H2 4N 204s 4 158927 C3H60 3 S

157298 C3 2H5 6 N204S4 159080 C1 3H28 N2S3

157310 C1 1 H1 5 IN2 S2 159083 C1 6 H1 7 N02 S

157311 C1 3 H2 7 NS2 159086 C1 7 H3 8 N2 04 SSi

157312 C1 4 H2 9 NS2 159087 C9 H2 0 N2 S 3

157402 C9 H2 2 NO4 PS 159088 C3 0 H2 8 N2 02 S 2

157408 C7 H1 7 N04 S2 159089 C9 H2 0 N2 S2

157148 C15H28N 2 159090 C7H15N0S 2

157529 C6 H16 N2S 159092 C9H1 9NOS 2

157736 C4 H9NO3S2 159094 C6HI3NO2S

157798 C1 2 H20 N20 3S2 159095 C6H1 3NO2 5

157799 CI5 H2 6N20 3S2 159096 C5H1 2 N2 S3

157841 C1 3 H2 7NS2 159098 C4 H9 NOS 3

157842 C1 3 H2 9N03S3 159240 C2 4H34 C14 N4 02S2

157843 C11 H2 3NS2 159241 C2 4H52 N2S2

157868 C17H24N20552 159242 C1 5H26 N2S

158490 C15 H2 3C1N 2S2 159243 C1 5H 2 7N2 0 3PS

842

WR No. Molecular Formula WR No. Molecular Formula

159244 C1 3 H2 9N04S2 162457 C7 H1 3NO3 S2

159245 C1 2 H 19C 2 N204 PS 162458 C3H8N2OS2

159246 C1 2H1 8 C12 N20S 162818 C 15H 22Cl 2N 2S2

159560 C1 40 2 6 N2 080 2 162857 C1 6 H2 8 C12 N2 S 2

159562 C1 3H2 1 NOS 162859 CH2NS

159567 C1 1H1 9 N3s 162860 C1lH 24 N2 S2

159568 ClIH 2 7 N2 03 PS 162862 C1 2 H1 7 1N2 S2

159569 ClOH1 8 N2 S2 162863 C1 4 H2 1 BrN2 S2

159570 c1OH23 N032 162864 C1 5 H2 3 BrN2 S 2

159573 C7 H1 6 N2 02 S 162865 C1 5 H2 3 lN 2 S2

159574 C1 2 H1 7 CIN2 S2 162866 C1 6 H2 5 1N 2 S2

159618 C1 2 H1 6 C12 N2 S2 165159 C6 H1 1 NO6 S 2

159619 C1 2 H1 7 BrN2 S2 165556 C1 3 H2 1 NOS

159620 C1 4 1R2 1 C1N2 OS 165560 C1 4 H2 6 NO4 PS

159621 C1 8 H2 9 BrN2 S 2 165561 C1 4 H2 5 NO4 S2

159742 C1 2 H2 6 NO3 PS 165563 C1 5 H2 8 N2 08 S2

159927 C7H1 5 NO4 S 165569 C1 7 H3 1 N3 04 S 2

159942 C1 4 H2 4 N2 0 3 S3 165571 C2 2 H5 0 N4 S2

159945 C1 0 H2 4 NO3 PS 165930 C9 H2 3 N2 03 PS

159947 C8 H2 1 N2 04 PS 165931 Cg9 H2 1 N2 03 PS

160442 C1 6H2 5 C1N2 S2 165932 C13 19NO

160452 C1 5 H2 6 BrN2 04 PS 166717 C1 2 H2 0 N2 0 3 S2

162452 C1 3 H2 8 N2 S2 166764 C22H42N452

162455 C9 H17 N03 S2 166817 CH 10N4S2

162456 C8 H1 5 NO3 S2 166818 C7 H16 N2 03 S2

843

WR No. Molecular Formula WR No. Molecular Formula

166820 C8 H1 6N20 3S2 169402 C1 4H2 7fN2 03PS

166822 C6H1 4 N20 3S2 169403 C2 8H4 6N4S4

166823 C1 0H2 2 N20 3 S2 169404 C7 H14 03 S2

166824 C1 oH2 1 N20 3PS 169413 C1 6H3 3NO2S3

166825 C1 0H2 oN2 S 169414 C24 H5 2 N2 S2 Zn

166826 C1lH 2 3NS2 169415 C1 0H2 1NO253

166827 C1 1 H2 3N2 03PS 169416 C9 H1 1 NO2S

166828 CllH2 2 N20 3S2 169417 C8 H1 7NO2 S2

166829 C1 1H2 2 N20 3 S2 169418 C7 H1 2N2 S

166830 C12 H2 5NS2 169419 C7 Hl5 NO2S3

166831 C1 2H24 N2 04 S2 169420 C6 H1 3NO2S3

166832 C 12H 20N2S 169422 C4H60 3S2

166834 C1 2H20 N2S 169423 C4 H7 C10 2 S2

166836 C1 3 H2 7NS2 170427 C7 H1 9N2 03PS

166839 C1 5H2 4N2S2 170432 C8 H2 1 N203PS

166840 C1 5H1 8N202S 170433 C8H1 2N2 05S3

166841 C1 6H3 0N4 S2 170439 C1 5H2 7N205PS

166842 C1 7H3 0N20 3S2 170440 C1 5H2 9N2 03PS

166843 C18 H34N 4 S2 170442 CloH15 N03S2

166847 C2 2H4 2N4 S2 170443 CllH2 0N20 5S2

166848 C22 H4 2N4 S2 170447 C1 7H3 2N3 04PS

166849 C24 H3 6 Br2 N40 2 S2 171079 C2 8H4 2N4S4

166850 C30 H50 N4 S2 171872 C1 4H26 NO4PS

167767 C6HllN0 3S2 171873 C1 4H2 5NO4S2

168643 C80 1 8 04S5 171888 C1 2H2 5N04 S2

844

WR No. Molecular Formula WR No. Molecular Formula

171889 C1 2 H2 6 N04 PS 176239 C9 H2 1 N2 03 PS

172689 CllH2 1 N2 05 PS 176240 C3 H1 oN3 03 PS

172729 C8 H1 8 N2 02 S 176241 C4 H1 2No5 PS

172730 C6 H1 7 N2 04 PS 176252 C1 6 H2 6 N20S

173113 C5 H1 1 NO2 S 3 176256 C8 H1 9 N2 0 3 PS

173114 C1 2 H2 8 N2 S2 Zn 176353 C1 4 H1 3 NO2 S

173116 C9 H1 9 NO2 S3 176357 C1 3 H1 5 NO2 S

173120 C2 4 H5 2 N2 NiS 2 176358 C1 2 H1 2 N2 02 S

173143 C4 H1 2 CdCI 4 N2 S2 176542 C6 H1 7 N2 0 3PS

173144 C4 H1 2 N2 PdS 2 176543 C1 0 H2 6 N2 08 P 2 S2

173145 C12H2NS 176606 C10llN 303S2

173151 C H 21N20 3PS 176610 C8 H1 0 N2 0S2

173312 C1 6 H2 9 F 3 N2 176611 C8 H1 8 N2 04 S2

174432 C1 6 H2 9 F3N2 176614 C7 H7 NS2

175811 C14 H2 0 N2 0 2 S4 176615 C1 2 H1 6 N6 S 2

175866 C2 4 H3 6 N2 0 2 S4 176617 C1 8 H2 0 N1 0 S2

175868 CI 2AI 6 N2 02 S4 176620 C1 7 H1 1 NS2

175874 C2 6 H2 8 N2 02 S4 176623 C1 2H1 4 N2 03 S2

175876 C2 0 H3 2 N202S 4 176634 C2 0 H2 0 N6 S 2

175877 C2 0 H3 2 N2 0 2 S2 176992 C1 9 H2 6 N2 s 2

175880 C1 4 H2 0 N2 0 2 S2 177471 C8 H1 7 N03S 2

175881 C12H N0S2 177472 C H NO S1216 2 22 8 17 3 2

176095 C3 2 H6 8 N2 S4 177473 C8 H1 7 NO3 S2

176176 C1 9 H2 1 CIN2 02 S 177474 C1 2 H2 4 N2 S2

176186 C8 HI 3 N05 S 177475 C1 2 H24N202S2

845

WR No. Molecular Formula VR No. Molecular Formula

177749 C1 4 B3 0 N4 S2 180038 C1 1 H1 4 N2 0 2 S

177481 C1 6 H3 2 N2 S2 180112 C8 H2 1 N2 03 PS

177577 C1 2 H2 1 NO7 S3 180148 C1 lH 1 0 NO6 PS

177581 C8 H1 2 06 S2 180152 C3 H1oN3 03 PS

177641 C6 H1 1 N04 S2 180548 C7 H1L3NS 2

177644 C6 H1 3 NO2 S2 181159 C1 0 H2 1 N02 S2

177645 CH11 NO2 2 181161 C6 H1 0NOPS 3

177646 C H 11NO 2S2 181162 C 13H 20N2S2

177647 C5 H1 1NO2 S2 181182 C1 4H2 2N2 0S2

177648 C4 H1 0N2 OS2 181183 C1 2 H1 8 N2 OS2

177649 C4 H9 NO2 S2 181187 C1 0 H1 4 N2 S2

177664 Cl1 H1 6N20S 2 181188 C20 H3 4 N2 S2

177665 C1 1 H1 8 N2 04 s 2 181189 C2 1 H3 6 N2 S2

177667 C 0 H1 4 N2 0S2 181190 C7 H1 7 N2 0sPS

17920? C5 111 5 N2 03 PS 181192 C9 H1 2N2S2

179210 C5H8F3 NOS 2 181193 C9 H14 NO2 PS 2

179212 C7 H2 0 N2 07 P2 S2 181194 C8HI 7N02S2

3.79213 C1 4 H2 5 NS 181195 C7H15 NO2 S2

179350 C1 6 H1804 S5 181196 C7H1 8NO2 PS

179351 C1 6 H2 601 2S5 181197 C6 H1 7 N202PS

179442 C12 H1 7NO3S3 181359 C5 H1 5N4 03PS

180034 C10H14 N 2S 181378 C6H 7N403PS

180035 C5 H 2N 2OS 181612 C2 6H4 2 N4S 2

180036 C4Io N2OS 181630 C3 H 7NS2

180037 C H 16N2OS 181640 C1 2H 18N202S2

846

WK No. Molecular Formula WR No. Molecular Formula

182141 C7 HI9N2 0 3 PS 186680 CllH1 5 N0 3 S

182619 C4 H1 1 NO3 S2 186682 C10 H1 3 NO3 S

183159 C1 2 H3 0 N4 S2 186683 CIOH2 4 NO2 PS3

183323 C16 H2 8 NO2 PS 2 186685 C9H7 NO2 S3

183324 C15 H2 1 NOS 2 186686 C9H7 N0 2 S2

183327 C1 4 H1 8 N2 02 S2 186688 C9 11NO3S

183328 C1 3 H1 7 NOS 2 186689 C8 H5 NO2 S 2

183329 C1 1H1 3NOS2 186691 C8 H2 1 N2 03 PS

183330 CloH2 0 N4 S3 186692 C6 H1 7 N06 S2

183331 C1 0 H1 9 NOS 2 186693 C6 H1 6 NO2 PS 3

183333 C9 H1 6 N2 0 2S 2 186697 c9H11NO3S2

183334 C8 H 5NOS2 187093 C H 17N 20 3Ps

183338 C6 H1 1 NOS 2 187094 C H 15N 20 3PS

183339 C6 H1 7 NO6 P 2S 187095 C1 6 H1 7 N03 S3

183368 C1 4 H2 8 N4 S3 187144 C2 4 H1 8 04 S5

183370 C7 H1 3 NOS 2 188300 C1 6 H1 5 C1 2 N03 S3

183372 C6 H1 2 N4 S 3 188301 C2 4 H1 4 C14 04 S5

183977 C7 H1 9 N2 03 PS 188440 C4 H9 NS

183978 C7 H1 9 N4 03 PS 189165 C1 6 H3 1 N02 S 4

183979 C7 Hl1 9 N40 3 PS 189169 ClI4H 1 9 N3 S3

184192 C1 1 H2 7 N2 03 PS 189172 C1 2 H1 5 N3 S3

186034 C2 0 H1 4 0 4 S5 189174 C H 3N 3S3

186675 C1 4 H1 6 NPS 3 189175 C1 oHI 1 N3 S3

186677 C3 H 9NO 3S 189176 C9 H1 7 N02 S4

186678 C1 2 H1 6 N2 04 S 189179 C7 H 1I 3 N02 S4

847

U No. Nolecular Formula WR No. Molecular Formula

189180 C5R9N02S4 193692 C1 6H2 3N2 0 3 PS

189196 C6 HIIN0 2 S4 193701 C6 H1 6 NO 3PS

190072 C H 23N20 3PS 193702 C6 H1 6 N2 S

190073 C7 H1 9 N2 04 PS 193704 C5 H1 4 NO3 PS

190189 C3 4 H6 7 N02 S 193706 C4 H1 2 NO3PS

190194 C 18H 37NOS 194423 C4 H1 3 N2 0 3 PS

190204 C1 3 H1 9 NO2 S 196264 C2 8 H4 6 N4 S 2

190205 C 13H 21NO2S 196265 C 24H 38N4S2

190206 C1 2 H1 9 NS 196267 CZOH4 2 N4 S2

190219 C8 H1 9 N2 05 PS 197486 C202002

190222 C7 H1 9 N4 03 PS 197487 C2 4 H4 2 N4 S 2

190282 C4 H9 NS 197490 C2 0 H3 8 N4 S2

192525 C5 H NS 197494 C1 6 H3 0 N4 S2

192526 C5 H NS 197499 C1 3 H1 4 N2 03 S2

192564 C2 4 H4 6 N4 S2 197500 c3H 4N 20 3S2

193677 C3 0 H 5 0N 4S 4 197511 C8 H1 6 N2 S

193678 C2 8 H4 6 N4S 4 197512 C8 H1 7 NS

193679 C2 6 H4 0 N2 04 S2 197516 C2 0 H3 4 N4 S 2

193681 C2 0 H3 8 N4 s 4 199268 C1 5 H2 6 N20 3 S 2

193682 C1 8 H3 4 N4 S2 199269 C3 0 H5 0 N4 S2

193684 C1 5 H2 6 N2 0 3 S3 199270 C2 8 H4 6 N4 S2

193685 C1 5 H2 1 N02 S 199271 C1 4 H2 4 N2 03 S2

193687 C1 4 H2 4 N203S 3 199275 C8 H2 1 N4 03 PS

193688 C1 4 H1 8 N2 0 3 S 199616 C1 6 H3 8 N8 S2

193690 C1 1 H1 3 NO2 S 199617 C3 4 H5 8 N4 S2

848

WR No. Molecular Formula WR No. Molecular Formula

199618 C3 2H5 4N4 S2 204011 C5H11NS

199631 C1 6H2 8N20 3S2 204157 C2 8H5 0 N4 S4

199634 C1 2H2 1 N20 3PS 204158 C1 5H28 N2 04 S2

199737 C26H26N4S2 204159 C1 4H2 6N2 03 S3

199739 C2 4 H4 2 N4 S 2 204163 C2 4 H4 6 N4 S4

199740 C2 4H4 6N4S2 204172 C1 2H2 4 N2 0353

199746 C1 8 H3 0 N4 S2 206036 C4 H9 N03 S2

199747 C1 8H3 0N4 S2 209449 C6H12 02 S2

199753 C9H1 9 NS3

199755 C5H1 1 NS3

199788 CllH2 0 N2S

199789 C7H15 NS3

201722 C2 4 H3 8N4 S2

201723 C20 H3 8N4S2

201724 C1 6H2 9NO3S2

201725 C3 6H6 2 N4 S2

201726 C3 4H5 8N4 S2

201727 C3 2H5 4 N4 S2

201728 C2 8H 4 6 N4 S2

201729 C1 8 H3 2N2 03S2

201730 C1 7H3 0N2 03 S2

201731 C1 6H2 9N203 PS

203923 C9H2 0 N20 2S

203924 C9H20 N2OS

203925 C8H18N20S

849

By Oider of the Beatay of the Amny

S. C. MEYKZtGaen, United Stat. Army

Official: ChieOf ofStaff

J. C. PZNNINGTONMqjor General, United Sat*# Army

The Adjutant General

U. S. GOVERNMENT PRINTING OrFFICE : 1979 0 - 303-"It

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