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Reactions of Some 1-Arylpiperazines and 1-Aryl-4-(2-Hydroxy-3

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Reactions of Some 1-Arylpiperazines and 1-Aryl-4-(2-Hydroxy-3 Reactions of Some l-Arylpiperazines and -Aryl-4- (2-Hydroxy-3-Methoxypropyl) Piperazines By HILDA HOWELL A DISSERTATION PRESENTED TO THE GRADUATE COUNQL OF THE UNIVERSITY OF FLORIDA IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY UNIVERSITY OF FLORIDA August, 1961 5 ACKNOWLEDGMENTS The author would like to thank Parke, Davis and Company who provided a graduate fellowship during part of this work. The able assistance of the faculty, staff, and fellow graduate students of the Chemistry Department has made this research quite pleasant. Thanks are also due to Miss Joan Merritt, Mrs. Marie Eckart, Mr. T. W. Brooks, and Mr. Ralph Damico for their help with the typing, drawings, and proofreading of this report. The special consideration of Mr. P. L. Bhatia who shared this laboratory is appreciated. Special recognition is offered to D». C. B. Smith, Commdr. N. L. Smith, Dr. W. M. Jones, and Dr. G. B. Butler, each of whom from his own ability and opportunity has been of inestimable help. The moral support of her parents, family, and friends has significantly contributed to the success of this graduate program. She is deeply indebted to Dr* C. B. Pollard for his inspiration and direction !n the early part of this work and to her graduate ccKnmittee for their friendship demonstrated particularly since his death. She is especially indebted to Dr. Harry H. Slsler for the under- standing way in which he has directed the completion of this research. His friexidship and encouragement have made graduate work an enjoyable experience. ^ TABLE OF CONTENTS Page ACKNOWLEDGMENTS. • ^* • II LIST OF TABLES iy ' CHAPTER -kr , I. INTRODUCTION. .... > * t * I XL. EXPERIMENTAL % • ^. Starting Materials • , Source of .... with . Reactioiis of l-Arylplperazines Benshydryl Chloride Reactioas of l»Aryl-4*(2-hyxi^<wy» 3-inethoxypropyl)pipe rassine . with Halogeziated Compouzids <, Ethers of , r ; Synthesis <rf Ben«hydryl . 1 •Aryl-4*(E-hydroxy« 3-methoxy» propyl)plperazine tZ m. GENERAL DISCUSSION It IV. SUMMARY 4S BIBLIOGRAPHY 44 BIOGRAPHICAL DATA 4? il UST OF TABLES TABLE Page 1. 1.ARYL.4-BENZHYDRYL PDPERAZINES ... 12 2. DEiaVATIVES OF l-ARyL^-(2-HYDilOXY- PROPYL)PIPERAZINES 15 CHAPTER I INTRODUCTION For thousands of years, man has separated materials from his natural environment and used them to alter the chemical or physical processes within his body. In general, these substances, known today as drugs or medicinal agents, may be said to have been used for their curative and protective powers against harmful substances within the body, for the elimination of parasitic organisms of both visible and microscopic sizes, or for the production of a desired level of sedation, anesthesia or hypnosis. The use of organic materials for this purpose dates from 12 3 the earliest history of medicine. The source of such drugs* »*•" was originally the extracts of certain familiar plants. For example, a Chinese herbal of the fifth century, B.C. , describes the hemp plant whose flowering top provided cannabis (marihuana), which the Chinese used as an anesthetic in surgery two thousand years ago. An authexkUc reference was made in the third century* B. C . , by Theophrastus to the juice of the poppy capsules from which opium is extracted. The antipyretic property of willow bark, from which salicin was later isolated, was known to the ancients. Colchicine, 2 found in the seeds of the autumn crocus of Asia Minor, was recommended in the sixth century, A.D. , for pain of articular origin. The powdered leaf of the foxglove was a source of digitalis and the leaves of a certain tree from the mountains of Peru and Bolivia still provide one of the sources of cocaine. The early European explorers of Brazil found ipecac ("Brazil root") used as an emetic agent. The root was later shown to contain the active agent emetine. The products of such plants as those yielding coffee, tea and cocoa are still used all over the world to provide beverages which contain caffeine or theobromine. The use of synthetic organic materials as therapeutic agents can probably be dated from the nineteenth century Mrlth the introduction of ether and chloroform as anesthetics. The knowledge of the chemistry of certain natural products acquired in the early development of the science quickly led to the use of other related natural substances, and subsequently to the isolation and synthesis illustrated <tf the active components of these products. This can be by the use of both willow and cinchona bark for antlpyrettc purposes and finally the isolation aiui characterisation of salicyl alcohol glucoside and the preparation of the related compound, acetylsalicyllc acldi? . This approach has led to a variety of researches which have resulted in the discovery and introduction of new therapeutic 3 materials. Some drugs* such as phenacetin, are developed as the result of observations of biological processes. Occasionally, as in the case of penicillin and of dramamine* discoveries are made accidentally by perceptive persons in the course of other vrork. Other compounds are examined because of their chemical relationship to active congeners. Sometimes, because compounds containing specific structural units have been shown to have certain desired physiological effects, compounds are synthesized with a specific purpose in mind. A few drugs such as qolnaerine (Atabrlne), chloroquine (Aralen) and chlorguanide (Paludrine) have come only from laborious screening processes having as tiieir objectives the discovery of compounds which satisfy a definite ne«d« - The purpose of the present research was to prepare several series of derivatives of piperasine with molecular structures containing arrangements of functional groups known to have pharmalogical activity as anthelmintic, antlhlstlminle and tranquilizing agents. The anthelmintic properties of piperazlne and its effectlvenes* against such parasites as ascarids and various oxyuridae is well known. The high level of filarial infestation of American military personnel while stationed in the western Pacific during World War U stimulated the research which resulted in the preparation of the highly effective diethylcarhamaziae hydrochloride (hetrazane) by ' diethylcarbamazine hydrochloride particularly those of the ethanol amine , . Hie aminoethers, serieSf have been used successfully as antihistimines. Compounds •".. .. •«, . f».-; » . having the general structure ; R-0-Cil|CH|^<R'R"» „ , .,:V^;:.- have been found to be especially effective antihistimines When R is ^* ^ the ben»hydryl group. Otiier active compounds *xe the benahydxyl or substituted benahydryl, derivatives of monosubstituted ^- - 'ty\,-:- -\ , ;v . : • x w.' piperaaines. , ; -i-.-A-r "''"^f .t , : • ...r ,, , Ar^CH-N S ^-R , ^ ? Later work** has Included such structural arrangements as " ' ' ' A-A R'-N\^S N-CR"R'"R'» R» = Carboxyalkyl R" = H or shortchain alkyl 5 R"'R'^ — giroaps which may, or may not, be aromatic In recent years, especially since 1957, there has been a widespread interest In similarly dlsubstltuted plperaslnes with respect to their effect on the central nervous system. Symmetrically substituted piperaBlnes of the type / \ 0{CH2)j^CH-N S N-CH(CH2)j^0 R R nrrOtolO R=lto8C atom alkyl use as as weU as their salts have been found to have therapeutic medullary depressamts, narcosis potentiators, and dilators of ^"^ cortical vessels. Derivatives of the following forms have been prepared for their properties in the treatment of hypertension and anxiety states: R — CH3, CjHj n 2 to 5 \ /— . (CH.) -N S N-R n = 2. 3 ^ V / \ , R-N S N-R' t ./^ W R = sabstitated benehydryl R« = CH2CH2OCH2CH2OH or C H^C H2OC H2C H2CX: H2CH2OH 21 A series of substituted phenylplperaeines which have been -'^ effective against progressive hypertension and hypertensive encephalopathy and which closely approximate the general structure oi some of the compounds prepared in the course of this research have the following formula. | ^ OR 2"5 = (CH2)30CH3. (CH2)20CH3 The compounds prepared in the present research corresponded to the following general formulas: I 7 OR' R-N s n-ch,chch,cx:h. and R-N S N-CH», R = phenyl or gubsUluted phenyl f • II li R' = CO-alkyl» C#, alkyl, benzyl, benzhydryl to Parke, All of these compounds are new and will be submitted Davis and Company for testing. CHAPTER n EXPERIMENTAL All yields reported in this chapter are based o& the reactaat present in the least stoichiometric quantity. AU temperatures refer to the centigrade scale and its symbol is omitted. Melting points are uncorrected. The elemental analyses were performed by Galbraith Liaboratories , Inc. « Knoxville* Tennessee. Source <d Starting Materials Several the substituted piperazines used in this research were unavailable from commercial sources and consequently were 22 * 23 prepared la this laboratory. The method of PolUrd, et al . , was used for the preparation of the N-phenylpiperazines bearing the following substituents on the phenyl giroup: 2-methyl-, 3-methyl-, 4-methyl-, 2-chloro-, 3-chloro-, and 4-chloro-. Those bearing the substituents 4-ethoxy-, 2-methyl- 3-chloro- » 2-methyl-5-chloro-, 2-chloro- 5 -methyl-, 3-chloro-4-metiiyl- were prepared according to Prolog, et al. as modified by Parcell. 8 - N- ( 2- Methox/phenyDpipe razine , N- ( 2-ethoxyphenyl) plperasine, N-CZ-ethylphenyDpipewiBine, and N-(2-propylthiophenyl)- piperaeine were fumUhfid as research samples by Parke, Davis and Company. The starting materials listed below were obtained Irom the commercial sources indicated and, unless otherwise
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