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Note | Regular issue | Vol 68, No. 2, 2006, pp.347-355
Published online, 27th December, 2005
DOI: 10.3987/COM-05-10609
Synthesis and Biological Evaluation of Benzothiazole Derivatives of Pyrimidines, Acrylonitriles, and Coumarins

Amal M. Youssef, Hany M. Mohamed, Caitlin Czezowski, Athar Ata, and Alaa S. Abd-El-Aziz*

*Department of Chemistry, The University of Winnipeg, 515 Portage Avenue, Winnipeg, Manitoba, R3B 2E9, Canada

Abstract

A number of benzothiazole derivatives of 2-aminopyrimidines (3a-b, 5, 6a-b, and 7), benzothiazole-3-arylacrylonitriles (10a-c), and benzothiazol-2-yl-coumarins (18a c, and 20) were synthesized by reacting benzothiazole derivatives with dicarbonyl compounds, and aromatic aldehydes. The unexpected 2-(4-methoxyphenyl)benzo[d]thiazole (14) was obtained as a unique product via the reaction of 2-aminothiophenol with ethyl 3-(4-methoxyphenyl)-2-scyanoacrylate. 2-(Benzo[d]thiazol-2-yl)-3-(4-hydroxyphenyl)acrylonitrile (10a) exhibited activity against Staphylococcus aureus. 2-(Benzo[d]thiazol-2-ylamino)pyrimidine-4,6-(1H,5H)-dione (3b) showed antibacterial activity selectivity against Corynebacterium xerosis. 2-(Benzo[d]thiazol-2-ylamino)-6-methylpyrimidin-4(3H)-one (5) showed weak anti-fungal activity against Candida albicans.