Application of Huisgen (3 + 2) cycloaddition reaction: Synthesis of 1-(2,3-dihydrobenzofuran-2-yl-methyl [1,2,3]-triazoles and their antitubercular evaluations

• Published in: European journal of medicinal chemistry Vol. 45; no. 1; pp. 142 - 148
• Main Authors: Tripathi, Rama P., Yadav, Amit Kumar, Ajay, Arya, Bisht, Surendra Singh, Chaturvedi, Vinita, Sinha, Sudhir Kumar
• Format: Journal Article
• Language: English
• Published: ISSY-LES-MOULINEAUX Elsevier Masson SAS 2010; Elsevier
• Subjects: 1,2,3-Triazoles; [3 + 2] cycloaddition; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antitubercular agents; Antitubercular Agents - chemical synthesis; Antitubercular Agents - chemistry; Antitubercular Agents - pharmacology; Biological and medical sciences; Chemistry, Medicinal; Cuprous iodide; Life Sciences & Biomedicine; Medical sciences; Microbial Sensitivity Tests; Mycobacterium tuberculosis - drug effects; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Science & Technology; Temperature; Triazoles - chemical synthesis; Triazoles - chemistry; Triazoles - pharmacology; 1,2,3-Triazoles; Cuprous iodide; Antitubercular agents; [3 + 2] cycloaddition; AZIDES; TRIAZOLE; POLYMER; CLICK; ALKYNES; EFFICIENT; [3+2] cycloaddition; 1,3-Dipolar cycloaddition; In vitro; Biological activity; Mycobacterium tuberculosis; Mycobacteriales; Mycobacteriaceae; Bacteria; Actinomycetes; Antituberculous agent; Benzofuran derivatives; Antibacterial agent; Chemical synthesis; Lipophilicity; Physicochemical properties
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2009.09.036

1,4-Disubstituted-1,2,3-triazoles ( 3– 27) have been synthesized by [3+2] cycloaddition of different 2-(azidomethyl)-dihydronaptho(benzo)furans ( 2a, 2b, 2c and 2d) with different alkynes. All the compounds were screened for antitubercular activity against Mycobacterium tuberculosis H 37Rv. Compounds 2a, 7, 9, 12 and 14 exhibited antitubercular activities with MIC ranging from 12.5 to 3.12 μg/ml. (3 + 2) Cycloaddition reaction of 2-azidomethyldihydrobenzofurans with different acetylenes gave 1-(2,3-dihydrobnzofuran-2-yl-methyl [1,2,3]-triazoles. The compounds were screened for their antitubercular activities. [Display omitted]