Synthesis and biological evaluation of 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thioglycosides |
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Authors: | Srikanth Vudhgiri Dhevendar Koude Dileep Kumar Veeragoni Sunil Misra RBN Prasad Ram Chandra Reddy Jala |
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Institution: | 1. Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India;2. Pharmacology & Toxicology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India;3. Academy of Scientific and Innovative Research, New Delhi, India |
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Abstract: | In the present study, the synthesis of 1, 3, 4-thiadiazole-based thioglycosides were accomplished in good yields with employing a convergent synthetic route. The starting material 5-amino-1, 3, 4-thiadiazole-2-thiol and followed by a series of 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thiols (4a–4j) were synthesized with different fatty acid chlorides. The glycosylation of compounds 4a–4j were achieved with trichloroacetimidate methodology. Antimicrobial and cytotoxicity activities of title compounds were evaluated. Among the entire compounds lauric acid and myristic acid derivatives showed good and moderate antimicrobial activity. In case of cytotoxicity results of compounds 8a–8j and 9a–9j, the acetate protected short chain (C6:0, C8:0, C10:0) compounds and the free hydroxyl long chain saturated (C16:0, C18:0) and unsaturated (C18:1, C22:1) compounds exhibited good activity against different cancer cell lines. Further, the free hydroxyl compounds 9a, 9c–9j did not show any toxicity towards normal CHO-K1 cell line whereas acylated compounds 8a–8j exhibited toxicity. |
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Keywords: | Fatty acids 1 3 4-Thiadiazole Thioglycoside Antimicrobial Cytotoxicity |
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