期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 20, 期 37, 页码 11685-11689出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201403560
关键词
alkynes; antiviral agents; cycloaddition; nucleosides; spiro compounds
资金
- University of Reading
- Syngenta
An efficient synthesis of spirocyclic triazolooxazine nucleosides is described. This was achieved by the conversion of beta-D-psicofuranose to the corresponding azido-derivative, followed by alkylation of the primary alcohol with a range of propargyl bromides, obtained by Sonogashira chemistry. The products of these reactions underwent 1,3-dipolar addition smoothly to generate the protected spirocyclic adducts. These were easily deprotected to give the corresponding ribose nucleosides. The library of compounds obtained was investigated for its antiviral activity using MHV (mouse hepatitis virus) as a model wherein derivative 3 f showed the most promising activity and tolerability.
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