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Title: | Synthesis and anticancer activity of 5-(3-indolyl)-1,3,4-thiadiazoles |
Authors: | Kumar, Dalip |
Keywords: | Chemistry 1,3,4-Thiadiazole Indolyl heterocycles Anticancer agents Indolyl azoles |
Issue Date: | Oct-2010 |
Publisher: | Elsiever |
Abstract: | A series of 5-(3-indolyl)-2-substituted-1,3,4-thiadiazoles 5a–m were synthesized and their cytotoxicity analyzed against six human cancer cell lines. The reaction of indole-3-carboxylic acid 3 with aryl or heteroaryl hydrazides afforded the N,N′-diacylhydrazines 4, which upon treatment with Lawesson’s reagent resulted in the formation of indolyl-1,3,4-thiadiazoles 5a–m in good yields. Indolyl-1,3,4-thiadiazole 5m with 4-benzyloxy-3-methoxyphenyl and 5-bromo indolyl substituents is the most active in suppressing the growth of cancer cells (IC50 1.5 μM, PaCa2). The compounds 5b, 5e and 5h bearing C-2 substituent as benzyl, 3,4-dimethoxyphenyl and 4-benzyloxy-3-methoxyphenyl, respectively, have shown significant cytotoxicity against multiple cancer cell lines. Introduction of 4-dimethylamino (5d and 5k) and 3,4,5-trimethoxy (5l) groups in the C-2 phenyl ring induced selectivity against MCF7 and MDA-MB-231 cancer cell lines (compounds 5d, 5k and 5l). |
URI: | https://www.sciencedirect.com/science/article/pii/S0223523410005039?via%3Dihub http://dspace.bits-pilani.ac.in:8080/xmlui/handle/123456789/3061 |
Appears in Collections: | Department of Chemistry |
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