Synthesis of (2-(phenylthio)phenyl)acetamidines and related amidoximes as potential antidepressants

Abstract

Reactions of ethyl(2-(phenylthio)phenyl)acetimidate (X) hydrochloride with ammonia and the corresponding amines resulted in amidines V-X. Heating (2-(phenylthio)phenyl)acetonitrile with 2-aminoethylammonium toluene-4-sulfonate led to the 2-imidazoline XI. Reactions of (2-(phenylthio)phenyl)acetonitrile and the lower homologue with hydroxylamine gave the amidoximes XIII and XV; XIII was oxidized to the sulfoxide XIV. Compounds VII, XI, and XIII showed some antireserpine activity which indicates thymoleptic and antidepressant potentiality. On the other hand, none of the compounds tested did show any noteworthy affinity to the [3H]imipramine and [3H]desipramine binding sites in the rat hypothalamus.