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. ORCID: https://orcid.org/0000-0001-6566-0155 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 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
URI	https://reading-clone.eprints-hosting.org/id/eprint/37264
Identification Number/DOI	10.1002/chem.201403560
Refereed	Yes
Divisions	Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) Life Sciences > School of Biological Sciences > Biomedical Sciences Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy > Medicinal Chemistry Research Group
Uncontrolled Keywords	alkynes;antiviral agents;cycloaddition;nucleosides;spiro compounds
Publisher	Wiley
Download/View statistics	View download statistics for this item