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

Abstract	Levamisole, the imidazo[2,1-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)-imidazo[2,1-b][1,3,4]thiadiazoles (SCR1), 2-aralkyl-5-bromo-6-(4'-fluorophenyl)-imidazo[2,1-b][1,3,4]-thiadiazoles (SCR2), 2-aralkyl-5-formyl-6-(4'-fluorophenyl)-imidazo[2,1-b][1,3,4]-thiadiazoles (SCR3) and 2-aralkyl-5-thiocyanato-6-(4'-fluorophenyl)-imidazo[2,1-b][1,3,4]-thiadiazoles (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 μM) 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.
Authors	Subhas S Karki, Kuppusamy Panjamurthy, Sujeet Kumar, Mridula Nambiar, Sureshbabu A Ramareddy, Kishore K Chiruvella, Sathees C Raghavan
Journal	European journal of medicinal chemistry (Eur J Med Chem) Vol. 46 Issue 6 Pg. 2109-16 (Jun 2011) ISSN: 1768-3254 [Electronic] France
PMID	21439690 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Copyright	Copyright © 2011 Elsevier Masson SAS. All rights reserved.
Chemical References	2-benzyl-5-thiocyanato-6-(4'-fluorophenyl)imidazo(2,1-b)(1,3,4)thiadiazole Antineoplastic Agents Imidazoles Thiadiazoles
Topics	Antineoplastic Agents (chemical synthesis, chemistry, pharmacology) Apoptosis (drug effects) Cell Proliferation (drug effects) Cell Survival (drug effects) Dose-Response Relationship, Drug Drug Screening Assays, Antitumor Humans Imidazoles (chemical synthesis, chemistry, pharmacology) Molecular Structure Stereoisomerism Structure-Activity Relationship Thiadiazoles (chemical synthesis, chemistry, pharmacology) Tumor Cells, Cultured

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