Arsenicals containing a pyridine nucleus PDF
Preview Arsenicals containing a pyridine nucleus
NOTE TO USERS This reproduction is the best copy available. UMI® Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. UNIVERSITY OF NEBRASKA LIBRARIES MANUSCRIPT THESIS Permission to use this thesis has been given by the author or department under whose direction it was written. Approved by author Approved by department............................................................................................................. It is expected that proper credit will be given for any quotations taken from this work. Extensive copying or publication of the thesis in whole or in part requires the written consent of the author or department. This thesis has been used by the following persons, whose signatures attest their accept ance of the above restrictions. A library which borrows this thesis for use by its patrons is expected to secure the signature of each user. NAME AND ADDRESS DATE Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. AJtttgBXWA oom* x s m a. . FXl'ISili StfftLSQS tff mmw% tm A fHMXt IfcOMbtod to tfe* Faoali y Of tho College la th# of letoraaka |» fovttox of lofofaoiaoata fo** the of Sootor of Philosophy Depa:.:— rtme^ n^—t■ JE ^. oMbr ©a unrtob~ ■ !m■ in ©x MsU -A&* jHafalkyMif Liaeola> Hebraska JToxmmuet 3JAS Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. UMI Number: DP13779 INFORMATION TO USERS The quality of this reproduction is dependent upon the quality of the copy submitted. 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Further reproduction prohibited without permission. *&i® author to his grntltwia to Br* ®* S* Kwiitim# UWM^LHfc^^fk- ro ^JBM-J-Ji w■*>- 515 fla* fTthf* *tJ»L* jH9L. ^ w @ #AfcW^ttk WMi*EIkwJ0*I frajMmwi Wi&9#i(M €^3l wt#jaa W[r .._ O--■* -Ea-a.* K^| » ^133 »v £^IliEP-ju *aN— %E ._■ —ttjt Satta and tapaagr for a research gjMiru&ajk smih sJLb* 396004 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. fable ©f ioaienta V tf* . X* Introduction . . . . . . . . . . . . . * . . . . . ' 1 XX* irej&jitaX lepreeentation of Ite&otioae* * * , * * * $ XXX* Discussion . . . . . . . . . . . . . . . . . . . . 7 If* BxperXffient&l * * * * * » . • • • » # » • « . . • * X® A# Preparation of 2-{p«araonophenylaraino)-3- nitr ©pyridine and related eoi8p©und8, * * * * * X® 1* 2 -Ohlor© ~$ «*ni tropyrldlne 2* 2-Cp~Aalnophenylaaino)-5-.nitropyrldin© 3. 2 - Cp-Arsonophenylintln©) *5 -nitr ©pyridine 4 * 2-(p -Ar ® enosophenylasiino} -5 -at tr ©pyridine S# 2-(p-Arsonopbienylaiaino)-S«a!ninopyridine 6* 4-£2* -(5* -AidinopyridylJJ-aialnophenyl- ar seal ©tie acid 1* freparatlon of 2 - (a-araonophenylaiaiBQ) -5 - ■ nitr ©pyridine and related oompsnmde* * * ♦ * .* li 7, 2-(««Jy®ln©phenyla®ln©) -S -nitropyridtne 8. 2*<m»Arsofnophenylamin©)-6-*nltropyrldine 9 • 2- (ei-Ar senosopiienyla®ino) ~S *ni tr ©pyridine 10* 2 - (m-Ar eonophenylamino} -5 -aainopyrt&ine #* Preparation of 2- (1* -benssotriaeolyl} -S-arsono- pyridine and related compomda # * * , , * * *. 21 11* 2- (o-Aiainopheaylsod.no) -5 -nitr ©pyridine 12. 2-(l*-Beneotriaeolyl)-5-nitropyridine 12* 2-(l* -Benaotriaaolyl)*5-aninopyrldlne 14* 2-cl*-Benaotriezolyl)-5-areonopyridlne IS. 2-fl1 -Benaotriaaolyl) -S-areenoaopyridine U* Preparation of 3-ni tro-4 - (p -arsonophenyl- anino)-pyridine and related compounds, * * * * 2§ 16 * Chelidonlc acid 17, Ohelidaxalc acid 18, The nitrate salt of 4-hydraxypyrldlne 19* 3 -Ifi tr © -4 -hydroxypyridlne 20, The hydrochloride of 3<-nitro*4<*©hl©r©- pyrldine 21 * 3 -N1 tr o-4 - (p -aminophenylamiao) -pyridine 22# 3-Hltro-4-ip-ar®«no|rib.ei»l»diio)-pyridine. 23, 4 - £4* - (3* -litropyridyl) J -amtnophenyl - arsaniouo aold Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. 1* "tatrodnotion 1 Since Shrlleh* e ayntkssi s of a^aphenajolii© the useful* ness of organic derivatives -of arseni© in'the "field-of chemotherapy has steadily-increased* However, Ike met'-of Many of such mwm&mX® is United because of Ike t«ati©iby* caused by their astiOn# toward the human system. 2a this connection the me# Of two organ!© arsenleala ■ will be briefly reviewed* • ■ Atm yl {Ike »«ao*e@ilw eell ©f p*e®la^toeiylttr»«ftie aeidj Is M©r® ©ff©otiv© th*** inorganic ' srsonlo In the tr®ati&tet of teypte©s©*®laai## However, Iks drug 1» espe* eially dangerous beoam®.® of ©file injury and blindness which result Mai il* use, ■ ■■ fiypsy§*SBid# (4 -arsonophenylglyoineamide), derived ■ t ■ trm at©*yl by Jacobs end B®id®ib©a?i©pf le need in the tr®at»««ib of' Idle central nervous. systte ■ syphilis m S in trypttoscwlasls* Cases of ©ft!©' injury and blindness have resulted also from the mm of Ibis tohpONMft* lino# no I*pyfiay!*4teiwaily*« of p~a»in©ph©nyi~ arsonle aeld have been reported in the literature ted be* d#-d cause Bins ted Balk ' have found that certain d-substi- ' luted derivatives of b«te*te©ffridi»® have therapeutic value It was the purpose of this investigatlte to study organ!© arsenical® of the following b|jt«#t 1. H-Pyrldyl- derivatives Of p-amlnophenyl&rson!e sold which also otetained a free ante©- gromp on the pyridine nuoleus* .§ Sinse the'.start of the investigation, infoi»ti« Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. t* , has been re©®fve4 to the effeeb that a m©lamia© dertw* ative of p •as&nophenylar sonie aeid width- probably ha® the following atnwetm1© H HHa a . . H /H=CV t O ' - w H MR* has been used affectively In the treatment of aleeping. sickness and 1a -reported to have little or no .,■■■. offset upon the ©ptie nerve* $* I~Pyridyl~ derivatives of m#easiao^enflar#oai« aeid abieh'alae have a free ipia® gritf on the pyridine. - aaelema* dliiioiigii it ie diffienlb to establish any tafalil* bl© rale*.'relating eihwalftaX e«etitatl* *»d therapeutic &et3 vity, ¥©mg and hoeventoart: observed that tonicity fw the opt!# nerve appear* to be connected with - the siiiatt tubed ante© group in. the pOeitfoa para* to the arsenic. Similar aoapoaariUi with the araenio in the ortho* or note* poeltioii are apparently free of thle danger* 3 . a *(i» • ^ a a o tria a ® ly l)* i« a r* « o ^ rid in e * Reproduced with permission of the copyright owner. Further reproduction prohibited without permission.
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