Synthesis and antiviral activity of novel spirocyclic nucleosidesElectronic supplementary information (ESI) available. CCDC 1840501 and 1840502. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8nj02777c
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 nucle...
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Zusammenfassung: | 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.
A diverse range of spirocyclic nucleosides have been prepared from a common precursor and tested for their antiviral activity. |
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ISSN: | 1144-0546 1369-9261 |
DOI: | 10.1039/c8nj02777c |