Synthesis and Antiviral Properties of Spirocyclic [1,2,3]‐Triazolooxazine Nucleosides |
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| Authors: | Antonio Dell'Isola Dr Matthew M W McLachlan Dr Benjamin W Neuman Hawaa M N Al‐Mullah Alexander W D Binks Warren Elvidge Dr Kenneth Shankland Dr Alexander J A Cobb |
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| Institution: | 1. School of Chemistry, Food and Pharmacy (SCFP), University of Reading, Whiteknights, Reading, Berks RG6 6AD (UK);2. Syngenta, Jealott's Hill International Research Centre, Bracknell, Berks RG42 6EY (UK);3. School of Biological Sciences, University of Reading, Whiteknights, Reading, Berks RG6 6AJ (UK) |
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| Abstract: | 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 by 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 3 f showed the most promising activity and tolerability. |
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| Keywords: | alkynes antiviral agents cycloaddition nucleosides spiro compounds |
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