127905-69-5Relevant articles and documents
POTENTIAL ANTIDEPRESSANTS: 2-(METHOXY- AND HYDROXY-PHENYLTHIO)BENZYLAMINES AS SELECTIVE INHIBITORS OF 5-HYDROXYTRYPTAMINE RE-UPTAKE IN THE BRAIN
Jilek, Jiri,Sindelar, Karel,Pomykacek, Josef,Kmonicek, Vojtech,Sedivy, Zdenek,et al.
, p. 3294 - 3338 (2007/10/02)
2-, 3- and 4-Methoxythiophenol, and 2,4-, 2,5- and 3,4-dimethoxythiophenol were transformed in two steps to the corresponding 2-(methoxyphenylthio)benzoyl chlorides XIII which were reacted with ammonia, methylamine, dimethylamine, diethylamine, dipropylamine, and di(2-propyl)amine to give the amides XIV-XIX.These were reduced mostly with lithium aluminium hydride to the amines II-VII.These methoxylated amines were demethylated mostly either by heating with pyridine hydrochloride or by treatment with boron tribromide.Some of the 2-(methoxy- and hydroxy-phenylthio)benzylamines prepared, especially compounds II, III, XXI, and XXII, indicated properties of potential antidepressants being highly active and selective inhibitors of 5-hydroxytryptamine re-uptake in the brain structures and having the typical antireserpine activity.The most interesting compound of the series is XXIb (hydrogen maleate VUFB-15 468) which is undergoing preclinical studies.On the basis of its structure, some further compounds (XXVII-XXIX, XXXIX-XLI) were prepared by various methods.
