title: Synthesis and antiviral properties of spirocyclic [1,2,3]-triazolooxazine nucleosides.
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.
authors.affiliation: School of Chemistry, Food and Pharmacy (SCFP), University of Reading, Whiteknights, Reading, Berks RG6 6AD (UK).
authors.forename: Antonio
authors.initials: A
authors.lastname: Dell'Isola
authors.forename: Matthew M W
authors.initials: MM
authors.lastname: McLachlan
authors.forename: Benjamin W
authors.initials: BW
authors.lastname: Neuman
authors.forename: Hawaa M N
authors.initials: HM
authors.lastname: Al-Mullah
authors.forename: Alexander W D
authors.initials: AW
authors.lastname: Binks
authors.forename: Warren
authors.initials: W
authors.lastname: Elvidge
authors.forename: Kenneth
authors.initials: K
authors.lastname: Shankland
authors.forename: Alexander J A
authors.initials: AJ
authors.lastname: Cobb
keywords: alkynes; antiviral agents; cycloaddition; nucleosides; spiro compounds
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