Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 24, Issue 8, Pages 1974-1979Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2014.02.061
Keywords
Adamantane; Triazoles; Click chemistry; Antitubercular activity; Mycobacterium tuberculosis
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Funding
- CSIR-12th FYP projects [CSC 0108, CSC0205, CSC0114]
- OSDD project [HCP0001, MLP0002]
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A series of novel 1,2,3-triazole-adamantylacetamide hybrids 5a-u, designed by combining bioactive fragments from antitubercular I-A09 and substituted adamantyl urea, were synthesized using copper catalyzed click chemistry. N-(1-Adamantyl)-2-azido acetamide 3 prepared from 1-adamantylamine was reacted with a series of alkyl/aryl acetylenes in the presence of copper sulfate and sodium ascorbate to give new analogues 5a-u in very good yields. Evaluation of all new compounds for in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv (ATCC27294), resulted N-(1-adamantan-1-yl)-2-(4( phenanthren-2-yl)-1H-1,2,3-triazol-1-yl) acetamide (5t) as most promising lead MIC: 3.12 mu g/mL) with selectivity index > 15. (C) 2014 Elsevier Ltd. All rights reserved.
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