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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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Publication details

The article was received on 04 Jun 2018, accepted on 13 Oct 2018 and first published on 17 Oct 2018


Article type: Paper
DOI: 10.1039/C8NJ02777C
Citation: New J. Chem., 2018,42, 18363-18380
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    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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