Journal
MEDICINAL CHEMISTRY RESEARCH
Volume 24, Issue 3, Pages 1298-1309Publisher
SPRINGER BIRKHAUSER
DOI: 10.1007/s00044-014-1210-y
Keywords
Carbazole; Triazole; Mycobacterium tuberculosis; Cycloaddition; Click chemistry; Cytotoxicity
Categories
Funding
- Crop Protection Chemicals Division, CSIR-IICT, Hyderabad, INDIA through CSIR-12th FYP Projects (ORIGIN) [CSC0108]
- UGC
- Crop Protection Chemicals Division, CSIR-IICT, Hyderabad, INDIA through CSIR-12th FYP Projects (DENOVA) [CSC0205]
- Crop Protection Chemicals Division, CSIR-IICT, Hyderabad, INDIA through CSIR-12th FYP Projects (IN-TELCOAT) [CSC0114]
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Herein, we describe synthesis and antitubercular evaluation of novel-substituted 1,2,3-triazolylmethyl carbazoles rationally designed by incorporating two pharmacophoric heterocycles, viz. carbazole and triazole in one molecular frame. The new compounds 4a-z and 4aa-ac were obtained in very good yields using copper-catalysed Huisgen [3 + 2] cycloaddition reaction of 9-propynyl-9H-carbazole (2) with various aryl/alkyl azides 3a-z and 3aa-ac. Evaluation of all 29 new analogues for in vitro antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv (ATCC 27294) resulted two compounds 4x and 4z (MIC: 6.25 mu g/mL) as most promising antitubercular agents with low cytotoxicity.
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