Synthesis and antiviral properties of spirocyclic [1,2,3]-triazolooxazine nucleosides. Academic Article uri icon


  • An efficient synthesis of spirocyclic triazolooxazine nucleosides is described. This was achieved by the conversion of -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 3f showed the most promising activity and tolerability.

published proceedings

  • Chemistry

author list (cited authors)

  • Dell'Isola, A., McLachlan, M., Neuman, B. W., Al-Mullah, H., Binks, A., Elvidge, W., Shankland, K., & Cobb, A.

citation count

  • 20

complete list of authors

  • Dell'Isola, Antonio||McLachlan, Matthew MW||Neuman, Benjamin W||Al-Mullah, Hawaa MN||Binks, Alexander WD||Elvidge, Warren||Shankland, Kenneth||Cobb, Alexander JA

publication date

  • September 2014