Synthesis and antidepressant evaluation of new 3-phenyl-5-sulfonamidoindole derivatives

Abstract

Ten new arylidenehydrazides were synthesized by reacting 3-phenyl-5-sulfonamidoindol-2-carboxylic acid hydrazide with various aldehydes and a new N-2-substituted hydrazide was prepared by reduction of 3-phenyl-5-sulfonamidoindole-2-carboxylic acid benzylidene-hydrazide 2 with sodium borohydride. The chemical structures of the compounds were verified by means of their IR, H-1-NMR, E1 mass spectroscopic data and elemental analyses. The antidepressant activity of these compounds were evaluated by the Porsolt forced swimming (behavioral despair) test using tranylcypromine as the standard. 3-Phenyl-5-sulfonamidoindole-2-carboxylic acid 3,4-methylenedioxybenzylidenehydrazide, 3-phenyl-5-sulfonamidoindole-2-carboxylic acid 4-methylbenzylidene- hydrazide, 3-phenyl-5-sulfonamidoindole-2-carboxylic acid 4-nitrobenzylidenehydrazide and 3-phenyl-5-sulfonamidoindole-2-carboxylic acid benzylidenehydrazide showed antidepressant activity at 100 mg/kg. (C) Elsevier, Paris.