Issue 2, 2018

Rapid synthesis of carbonucleoside phophonate analogues as potential antiviral agents via a hydrophosphonylation reaction of ethynyl 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.

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

Supplementary files

Article information

Article type
Paper
Submitted
16 Oct 2017
Accepted
06 Dec 2017
First published
06 Dec 2017

New J. Chem., 2018,42, 974-979

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

B. Sidi Mohamed, C. Périgaud, S. Peyrottes, J. Uttaro and C. Mathé, New J. Chem., 2018, 42, 974 DOI: 10.1039/C7NJ03991C

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