46708-52-5Relevant academic research and scientific papers
POTENTIAL ANTIDEPRESSANTS: 2-(PHENYLTHIO)ARALKYLAMINE
Jilek, Jiri,Urban, Jiri,Taufmann, Petr,Holubek, Jiri,Dlabac, Antonin,et al.
, p. 1995 - 2008 (2007/10/02)
Reactions of 2-(phenylthio)benzyl chloride with dimethylamine, diethylamine, pyrrolidine, piperidine, morpholine, and 1-methylpiperazine afforded the title compounds VI-XI.Reaction of 2-(phenylthio)benzaldehyde with nitromethane gave the nitrostyrene XIV which was reduced with lithium aluminium hydride to 2-(2-phenylthio)phenyl)ethylamine (XVI).This was transformed to the N-methyl and N,N-dimethyl derivatives XVIII and XIX.The Claisen reaction of (2-(2-phenylthio)phenyl)acetonitrile with ethyl acetate afforded the compound XXI which was cleaved by phosphoric acid to (2-(phenylthio)phenyl)acetone (XX).The Leuckart-Wallach reaction afforded the formamide XXIII which was used as starting material for preparing the amines XXIV-XXVI.The alternative approach to these compounds starting by reaction of the aldehyde XII with nitroethane was complicated by the fact that in addition to the nitropropene XV 2-(phenylthio)benzonitrile was also formed.The synthetic use of the inhomogenous XV resulted then in mixtures of amines XXIV-XXVI with IV-VI which was followed by means of mass and 1H NMR spectra.The amines XXIV-XXVI were oxidized to the sulfoxides XXVII-XXIX.The oily bases were transformed to crystalline salts and spectra of all homogeneous bases were recorded.Pharmacological testing showed the amine VI (VUFB-15370) to be a promising potential antidepressant.The amines XI and XXV showed also pharmacological profile of potential antidepressant.
Phenylthioaralkylamines
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, (2008/06/13)
Phenylthioaralkylamines and 2-phenylthiobenzylamines are prepared by reaction of the corresponding phenylthiobenzoyl chloride or homologs thereof with ammonia or an amine to produce the corresponding phenylthiobenzamide or N-substituted or N,N-disubstitut
