Preparation and reactions of sugar azides with alkynes: synthesis of sugar triazoles as antitubercular agents |
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Authors: | Singh Biswajit Kumar Yadav Amit Kumar Kumar Brijesh Gaikwad A Sinha Sudhir Kumar Chaturvedi Vinita Tripathi Rama Pati |
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Institution: | Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow 226 001, India. |
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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. |
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Keywords: | 1 3-Cycloaddition Glycosyl azide Sugar triazole Sodium ascorbate |
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