Document Detail


Preparation and reactions of sugar azides with alkynes: synthesis of sugar triazoles as antitubercular agents.
MedLine Citation:
PMID:  18346719     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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:
Biswajit Kumar Singh; Amit Kumar Yadav; Brijesh Kumar; A Gaikwad; Sudhir Kumar Sinha; Vinita Chaturvedi; Rama Pati Tripathi
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Publication Detail:
Type:  Journal Article     Date:  2008-02-20
Journal Detail:
Title:  Carbohydrate research     Volume:  343     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  2008 May 
Date Detail:
Created Date:  2008-04-18     Completed Date:  2008-07-28     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  1153-62     Citation Subset:  IM    
Affiliation:
Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow 226 001, India.
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MeSH Terms
Descriptor/Qualifier:
Alkynes / chemistry*
Antitubercular Agents / chemical synthesis*,  pharmacology
Azides / chemistry*
Carbohydrates / chemistry*
Cyclization
Microbial Sensitivity Tests
Molecular Structure
Mycobacterium tuberculosis / drug effects
Structure-Activity Relationship
Triazoles / chemical synthesis*
Chemical
Reg. No./Substance:
0/Alkynes; 0/Antitubercular Agents; 0/Azides; 0/Carbohydrates; 0/Triazoles

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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