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Synthesis and biological evaluation of novel 2-aralkyl-5-substituted-6-(4 `-fluorophenyl)-imidazo2,1-b]1,3,4]thiadiazole derivatives as potent anticancer agents

Karki, Subhas S and Panjamurthy, Kuppusamy and Kumar, Sujeet and Nambiar, Mridula and Ramareddy, Sureshbabu A and Chiruvella, Kishore K and Raghavan, Sathees C (2011) Synthesis and biological evaluation of novel 2-aralkyl-5-substituted-6-(4 `-fluorophenyl)-imidazo2,1-b]1,3,4]thiadiazole derivatives as potent anticancer agents. In: European Journal of Medicinal Chemistry, 46 (6). pp. 2109-2116.

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Official URL: http://dx.doi.org/10.1016/j.ejmech.2011.02.064


Levamisole, the imidazo2,1-b]thiazole derivative has been reported as a potential antitumor agent. In the present study, we synthesized, characterized and evaluated biological activity of its novel analogues with substitution in the aralkyl group and on imidazothiadiazole molecules with same chemical backbone but different side chains namely 2-aralkyl-6-(4'-fluorophenyl)-imidazo2,1-b]1,3,4]thiadiazoles (SCR1), 2-aralkyl-5-bromo-6-(4'-fluorophenyl)-imidazo2,1-b]1,3,4]-thiadiaz oles (SCR2), 2-aralkyl-5-formyl-6-(4'-fluorophenyl)-imidazo2,1-b]1,3,4]-thiadia zoles (SCR3) and 2-aralkyl-5-thiocyanato-6-(4'-fluorophenyl)-imidazo2,1-b]1,3,4]-th iadiazoles (SCR4) on leukemia cells. The cytotoxic studies showed that 3a, 4a, and 4c exhibited strong cytotoxicity while others had moderate cytotoxicity. Among these we chose 4a (IC50, 8 mu M) for understanding its mechanism of cytotoxicity. FACS analysis in conjunction with mitochondrial membrane potential and DNA fragmentation studies indicated that 4a induced apoptosis without cell cycle arrest suggesting that it could be used as a potential chemotherapeutic agent. (C) 2011 Elsevier Masson SAS. All rights reserved.

Item Type: Journal Article
Publication: European Journal of Medicinal Chemistry
Publisher: Elsevier Science
Additional Information: Copyright of this article belongs to Elsevier Science.
Keywords: Anticancer drugs;Cancer therapeutics;Cytotoxicity;Double-strand breaks;Apoptosis;Cell death
Department/Centre: Division of Biological Sciences > Biochemistry
Date Deposited: 22 Jun 2011 09:29
Last Modified: 22 Jun 2011 09:29
URI: http://eprints.iisc.ac.in/id/eprint/38425

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