title: Preparation and reactions of sugar azides with alkynes: synthesis of sugar triazoles as antitubercular agents.
abstract: 5-azido-5-deoxy-xylo-, ribo-, and arabinofuranoses were prepared by the reaction of the respective 5-O-(methanesulfonyl) or p-toluenesulfonyl derivatives with NaN3 in DMF. The intermediate 5-azido-5-deoxy glycofuranoses on 1,3-cycloaddition with different alkynes in the presence of CuSO4 and sodium ascorbate gave the corresponding sugar triazoles in very good yields. The synthesized sugar triazoles were evaluated for their antitubercular activity against Mycobacterium tuberculosis H37Rv, where one of the compounds displayed mild antitubercular activity in vitro with MIC 12.5 microg/mL.
authors.affiliation: Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow 226 001, India.
authors.forename: Biswajit Kumar
authors.initials: BK
authors.lastname: Singh
authors.forename: Amit Kumar
authors.initials: AK
authors.lastname: Yadav
authors.forename: Brijesh
authors.initials: B
authors.lastname: Kumar
authors.forename: A
authors.initials: A
authors.lastname: Gaikwad
authors.forename: Sudhir Kumar
authors.initials: SK
authors.lastname: Sinha
authors.forename: Vinita
authors.initials: V
authors.lastname: Chaturvedi
authors.forename: Rama Pati
authors.initials: RP
authors.lastname: Tripathi
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001386:Azides / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D003500:Cyclization; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000138:chemical synthesis*
chemical_list: D000480:Alkynes; D000995:Antitubercular Agents; D001386:Azides; D002241:Carbohydrates; D014230:Triazoles