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Issue 22, 2018
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Synthesis and antiviral activity of novel spirocyclic nucleosides

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Abstract

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.

Graphical abstract: Synthesis and antiviral activity of novel spirocyclic nucleosides

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Supplementary files

Article information


Submitted
04 Jun 2018
Accepted
13 Oct 2018
First published
17 Oct 2018

New J. Chem., 2018,42, 18363-18380
Article type
Paper

Synthesis and antiviral activity of novel spirocyclic nucleosides

A. J. A. Cobb, A. Dell’Isola, B. O. Abdulsattar, M. M. W. McLachlan, B. W. Neuman, C. Müller, K. Shankland, H. M. N. Al-Mulla, A. W. D. Binks and W. Elvidge, New J. Chem., 2018, 42, 18363 DOI: 10.1039/C8NJ02777C

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