SYNTHESIS, ANTIMICROBIAL AND ANTIOXIDANT ACTIVITIES OF SOME NOVEL -N-[(5-SUBSTITUTED-2-PHENYL-1H-INDOL-3-YL) METHYLENE]-4-PHENYLTHIAZOL-2-AMINE DERIVATIVES

Abstract

A series of new N-[(5-substituted -2-phenyl-1H-indol-3-yl) methylene]-4-phenylthiazol-2-amines (3a-c) have been prepared by cyclocondensation of 2-amino-4-phenylthiazole (1) with 5-substituted 2-phenyl-1H-indo1-3-carbaldehydes (2a-c). Compounds (3a-c) were subjected to cyclocondensation with thioglycollic acid, phenyl acetylchloride and chloroacetyl chloride to yield 2-(5-substitted-2-phenyl-1H-indo1-3-yl)-3-(4-phenylthiazol-2-yl)thiazolidin-4-ones (4a-c), 4-(5-substituted-2-phenyl-1H-indol-3-yl)-3-phenyl-1-(4-phenylthiazol-2-yl) azetidin-2-ones (5a-f). Compounds (3a-c) on reaction with substituted diazotised anilines yielded N-(4-substituted phenylimino)-5-substituted 2-phenyl-N'-(4-phenylthiazol-2-yl)-1H-indol-3-carboxamidines (6a-i). The synthesized compounds have been screened for their antimicrobial activity against E. coli, B. subtilis and K. pneumoniae and for antifungal activity against A. niger, A. flavus and A. fumigatus. Some of the compounds displayed pronounced antimicrobial and antioxidant activities.