Synthesis and anti-inflammatory activity of indolyl azetidinones.

Abstract

N- (3-chloro-2-oxo-4-phenyl-1-azetidinyl)-4-[4,5-dihydro - 4 (1H - indolyl-3-yyl methylene)-2-methyl-5-oxo-1H-imidazol-1-yl-(substituted benzylidene)] benzamides (VIa-i) have been prepared by the condensation of N-(3-chloro-2-oxo-4-phenyl-1-azetidinyl)-4-[4,5-dihydro-(1H-indol-3-yl -methylene)-2 - methyl-5oxo - 1H- imidazol-1-yl] benzamides (Va-c) with aryl aldehydes. The azetidinones in turn have been obtained by the reaction of corresponding hydrazones (IVA-c) with chloro acetyl chloride. The different substituted hydrazones (IVA-c) have been prepared by the reaction of 4- (1H-indol-3-yl-methylene)-2-methyl-5-(4H)-oxazolone (I) with methyl 4-amino benzoate followed by hydrazine hydrate and appropriate aldehydes. All the compounds were tested for their anti-inflammatory activity. The most active compounds were compared for their anti-inflammatory and ulcerogenic activities with non-steroidal anti-inflammatory drugs (NSAIDS).