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The Synthesis and Cytotoxicity of Novel Thiophene Derivatives Derived from 2-(4-Oxo-4,4-Dihydrothiazol-2-yl) Acetonitrile
National Organization for Drug Control & Research (NODCAR), Cairo, Egypt
Department of Pharmaceutical Chemistry, College of Pharmacy, University of Hail, Hail, Kingdom of Saudi Arabia
National Organization for Drug Control & Research (NODCAR), Cairo, Egypt
- 1 National Organization for Drug Control & Research (NODCAR), Cairo, Egypt
- 2 Department of Pharmaceutical Chemistry, College of Pharmacy, University of Hail, Hail, Kingdom of Saudi Arabia
- 3 National Organization for Drug Control & Research (NODCAR), Cairo, Egypt
International Journal of Organic Chemistry·Volume 06 (2016)·Pages 85–94·Published 19 May 2016·DOI10.4236/ijoc.2016.62009
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Abstract
The reaction of the 2-(4-oxo-4,4-dihydrothiazol-2-yl)acetonitrile 1 with cyaclopentanone (2) afforded the condensed product 3. The latter underwent a series of heterocyclizations through its reaction with different reagents. Moreover, compound 1 underwent the Gewald’s thiophene to afford compounds 15 and 17. The reaction of either hydrazine hydrate or phenylhydrazine with compound 17 gave the hydrazide derivatives 19a and 19b, respectively. The cytotoxicity of the newly synthesized products was measured towards the three cancer cell lines MCF-7, NCI-H460 and SF-268. The study showed that compounds 3, 5, 9c, 11, 13a, 13c, 17 and 19b were the most active compounds towards the three cancer cell lines.
KeywordsThiazoleCyclopentanoneThiopheneHydrazideCytotoxicity
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