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. ORCID: https://orcid.org/0000-0001-6566-0155, 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 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
URI	https://reading-clone.eprints-hosting.org/id/eprint/80622
Identification Number/DOI	10.1039/c8nj02777c
Refereed	Yes
Divisions	Life Sciences > School of Biological Sciences Life Sciences > School of Chemistry, Food and Pharmacy
Uncontrolled Keywords	Materials Chemistry, General Chemistry, Catalysis
Publisher	Royal Society of Chemistry
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