Rapid synthesis of carbonucleoside phophonate analogues as potential antiviral agents via a hydrophosphonylation reaction of ethynyl carbocyclic precursors?

New Journal of Chemistry Pub Date: 2017-12-06 DOI: 10.1039/C7NJ03991C

Abstract

A racemic synthesis of new carbocyclic nucleoside ethyl or vinylphosphonate analogues bearing purine bases (adenine and guanine) was accomplished using racemic (+/?)-4-O-protected-2-cyclopentanone. All compounds were prepared using a hydrophosphonylation reaction of ethynyl carbocyclic precursors followed by a Mitsunobu coupling reaction between the heterocyclic bases. After deprotection, the compounds were evaluated for their activity against a large number of viruses. However, none of them showed significant antiviral activity or cytotoxicity.

Graphical abstract: Rapid synthesis of carbonucleoside phophonate analogues as potential antiviral agents via a hydrophosphonylation reaction of ethynyl carbocyclic precursors
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