Synthesis of 3-heteroarylthioquinoline derivatives and their in?vitro antituberculosis and cytotoxicity studies

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• 作者：Selvam Chitra^a ; Nidhin Paul^b ; Shanmugam Muthusubramanian^b ; ^{muthumanian2001@yahoo.com} ; Paramasivam Manisankar^a ; ^{pms11@rediffmail.com} ; Perumal Yogeeswari^c ; Dharmarajan Sriram^c
• 关键词：Friedlander annulation ; Thiadiazole ; Benzo[d]thiazole ; Tetrazole ; Antimycobacterial activity ; Mycobacterium tuberculosis
• 刊名：European Journal of Medicinal Chemistry
• 出版年：2011
• 出版时间：October, 2011
• 年：2011
• 卷：46
• 期：10
• 页码：4897-4903
• 全文大小：608 K

文摘

A series of 3-heteroarylthioquinoline derivatives has been synthesized by the Friedlander annulation of 2-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-1-aryl-1-ethanone/2-(1,3-benzothiazol-2-ylsulfanyl)-1-aryl-1-ethanone/1-aryl-2-[(2-phenyl-2H-1,2,3,4-tetraazol-5-yl)sulfanyl]-1-ethanone with 2-aminobenzophenone in good yields using YbCl₃ as the catalyst. These compounds have been screened for their in?vitro activity against Mycobacterium tuberculosis H37Rv (MTB) and among the 21 compounds screened, 2-[2-(4-bromophenyl)-4-phenyl-3-quinolyl]sulfanyl-5-methyl-1,3,4-thiadiazole (5d) and 2-[2-(4-chlorophenyl)-4-phenyl-3-quinolyl]sulfanyl-5-methyl-1,3,4-thiadiazole (5c) were found to be the most active compounds with MIC of 3.2 and 3.5?¦ÌM respectively against MTB. The cytotoxic effects against mouse fibroblasts (NIH 3T3) in?vitro were evaluated for 5c and 5d, which displayed no toxic effects (IC₅₀?>?1000?¦ÌM) against the mouse fibroblast cell line NIH 3T3.