Preparation and reactions of sugar azides with alkynes: synthesis of sugar triazoles as antitubercular agents.
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.
Singh
Biswajit Kumar
BK
Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow 226 001, India.
Yadav
Amit Kumar
AK
Kumar
Brijesh
B
Gaikwad
A
A
Sinha
Sudhir Kumar
SK
Chaturvedi
Vinita
V
Tripathi
Rama Pati
RP
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*
D000480:Alkynes; D000995:Antitubercular Agents; D001386:Azides; D002241:Carbohydrates; D014230:Triazoles