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Synthesis and antiviral activity of novel spirocyclic nucleosides

Cobb, A. J. A., Dell’Isola, A., Abdulsattar, B. O., McLachlan, M. M. W., Neuman, B. W., Müller, C., Shankland, K., Al-Mulla, H. M. N., Binks, A. W. D. and Elvidge, W. (2018) Synthesis and antiviral activity of novel spirocyclic nucleosides. New Journal of Chemistry, 42 (22). pp. 18363-18380. ISSN 1144-0546

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To link to this item DOI: 10.1039/c8nj02777c

Abstract/Summary

The synthesis of a number of spirocyclic ribonucleosides containing either a triazolic or azetidinic system is described, along with two analogous phosphonate derivatives of the former. These systems were constructed from the same β-D-psicofuranose starting material. The triazole spirocyclic nucleosides were constructed using the 1-azido-1-hydroxymethyl derived sugars, where the primary alcohol was alkylated with a range of propargyl bromides, whereas the azetidine systems orginated from the corresponding 1-cyano-1-hydroxymethyl sugars. Owing to their close similarity with ribavirin, the library of compounds were investigated for their antiviral properties using MHV (Murine Hepatitis Virus) as a model.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Biological Sciences
Faculty of Life Sciences > School of Chemistry, Food and Pharmacy
ID Code:80622
Uncontrolled Keywords:Materials Chemistry, General Chemistry, Catalysis
Publisher:Royal Society of Chemistry

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