Synthesis and antiviral activity of novel spirocyclic nucleosides. (23rd October 2018)

• Record Type: Journal Article
• Authors: Cobb, Alexander J. A.; Dell'Isola, Antonio; Abdulsattar, Ban O.; McLachlan, Matthew M. W.; Neuman, Benjamin W.; Müller, Christin; Shankland, Kenneth; Al-Mulla, Hawaa M. N.; Binks, Alexander W. D.; Elvidge, Warren
• Is Part Of: New journal of chemistry. Volume 42:Number 22(2018)
• Page Start: 18363
• Page End: 18380
• Publication Date: 2018-10-23
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c8nj02777c
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : A diverse range of spirocyclic nucleosides have been prepared from a common precursor and tested for their antiviral activity. 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.