Rapid synthesis of carbonucleoside phophonate analogues as potential antiviral agents via a hydrophosphonylation reaction of ethynyl carbocyclic precursors. (12th December 2017)

• Record Type: Journal Article
• Authors: Sidi Mohamed, Bemba; Périgaud, Christian; Peyrottes, Suzanne; Uttaro, Jean-Pierre; Mathé, Christophe
• Is Part Of: New journal of chemistry. Volume 42:Number 2(2018)
• Page Start: 974
• Page End: 979
• Publication Date: 2017-12-12
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c7nj03991c
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : Carbonucleoside phosphonate analogues were readily obtained using a free-radical hydrophosphonylation reaction under UV/Vis light irradiation of alkyne carbocyclic precursors. 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.