Antimicrobial activities of some novel thiazoles

Abstract

2-(4-Phenylthiazol-2(3H)-ylidene)-malononitrile was synthesized by treating 1-phenyl-2-thiocyanatoethanone with malononitrile. Reaction of 2-(4-phenylthiazol-2(3H)-ylidene)-malononitrile with hydrazine hydrate afforded 4-(4-phenylthiazol-2-yl)-1H-pyrazole-3,5-diamine, reaction with benzylidenemalononitrile yielded 2-(5-benzylidene-4-phenyl-5H-thiazol-2-ylidene)-malononitrile, and coupling with benzenediazonium chloride gave 2-(4-phenyl-5-phenylazo-3H-thiazol-2-ylidene)-malononitrile. Diaminopyrazole reacted with enaminonitrile to yield the 3-(4-phenylthiazol-2-yl)pyrazolo[1,5-a]pyrimidine-2,7-diamine. All synthesized compounds showed significant antimicrobial activities with MIC range of 5–750 µg/mL. The results demonstrated a correlation of the hydrophobicity of the compounds with their antimicrobial activity. The most potent antimicrobial compound was 2-(4-phenylthiazol-2(3H)-ylidene)-malononitrile.