Design, synthesis and in vitro anti-tuberculosis activity of benzo[6,7]cyclohepta[1,2-b]pyridine-1,2,3-triazole derivatives

• Published in: Bioorganic & medicinal chemistry letters 2017-12, Vol.27 (23), p.5119-5121
• Main Authors: Sajja, Yasodakrishna, Vanguru, Sowmya, Vulupala, Hanmanth Reddy, Bantu, Rajashaker, Yogeswari, Perumal, Sriram, Dharmarajan, Nagarapu, Lingaiah
• Format: Article
• Language: English
• Subjects: Antitubercular Agents - chemical synthesis; Antitubercular Agents - pharmacology; Antitubercular Agents - toxicity; Benzo[6,7]cyclohepta[1,2-b]pyridine; Cell Survival - drug effects; Click reaction; Drug Design; HEK293 Cells; Humans; Microbial Sensitivity Tests; Mycobacterium tuberculosis; Mycobacterium tuberculosis - drug effects; Pyridines - chemistry; Structure-Activity Relationship; Triazole; Triazoles - chemistry; Triazoles - pharmacology; Triazoles - toxicity
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2017.10.071

[Display omitted] A series of novel benzo[6,7]cyclohepta[1,2-b]pyridine-1,2,3-triazole hybrids (7a–j &8a–j) have been designed and synthesized in excellent yields by Huisgen’s [3+2] cyclo addition reaction of 3-(azidomethyl)-2-methyl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridine (5) with various alkynes 6 in presence of copper sulphate and sodium ascorbate and their structures were confirmed by IR, 1H NMR, 13C NMR and HRMS. The newly synthesized compounds 7a–j &8a–j were evaluated for their in vitro anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv (ATCC 27294). Among the compounds tested, the compounds 7i and 8g displayed most potent activity with MIC value of 1.56 µg/mL with low cytotoxicity.