ANTIMICROBIAL ACTIVITIES OF SOME NOVEL THIAZOLES
© 2016 Saleh M. Al-Mousawi*, #, Moustafa Sherief Moustafa**, and Esmaeil Al-Saleh**
*Department of Chemistry, Faculty of Science, University of Kuwait, Safat, 13060 Kuwait; **Department of Biological Sciences, Faculty of Science, University of Kuwait, Safat, 13060 Kuwait
Received December 25, 2015; in final form, February 2, 2016
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.
Keywords: thiazoles, aminopyrazoles, antimicrobia activities.
Биоорг. химия 2016, 42 (4): 475-480