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Synthesis and antiviral properties of spirocyclic [1,2,3]-triazolooxazine nucleosides

Dell'Isola, A., McLachlan, M. M. W., Neuman, B. W., Al-Mullah, H. M. N., Binks, A. W. D., Elvidge, W., Shankland, K. and Cobb, A. J. A. (2014) Synthesis and antiviral properties of spirocyclic [1,2,3]-triazolooxazine nucleosides. Chemistry- A European Journal, 20 (37). pp. 11685-11689. ISSN 0947-6539

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To link to this item DOI: 10.1002/chem.201403560

Abstract/Summary

An efficient synthesis of spirocyclic triazolooxazine nucleosides is described. This was achieved by the conversion of β-D-psicofuranose to the corresponding azido-derivative, followed by alkylation of the primary alcohol with a range of propargyl bromides - obtained via 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 3f showed the most promising activity and tolerability.

Item Type:Article
Refereed:Yes
Divisions:Interdisciplinary centres and themes > Chemical Analysis Facility (CAF)
Faculty of Life Sciences > School of Biological Sciences > Biomedical Sciences
Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy > Medicinal Chemistry Research Group
ID Code:37264
Uncontrolled Keywords:alkynes;antiviral agents;cycloaddition;nucleosides;spiro compounds
Publisher:Wiley

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