Issue 12, 2003

Synthesis and antiviral evaluation of 2′-deoxy-2′-C-trifluoromethyl β-d-ribonucleoside analogues bearing the five naturally occurring nucleic acid bases

Abstract

2′-Deoxy-2′-C-trifluoromethyl-β-D-ribonucleoside derivatives bearing the five naturally occurring acid bases have been synthesized. All these derivatives were prepared by glycosylation reactions of purine and pyrimidine bases with a suitable peracylated 2-deoxy-2-C-trifluoromethyl sugar precursor to afford anomeric mixtures of protected nucleosides. After separation and deprotection, the resulting β-nucleoside analogues were tested for their activity against HIV, HBV and several RNA viruses. However, none of these compounds showed significant antiviral activity nor cytotoxicity.

Graphical abstract: Synthesis and antiviral evaluation of 2′-deoxy-2′-C-trifluoromethyl β-d-ribonucleoside analogues bearing the five naturally occurring nucleic acid bases

Article information

Article type
Paper
Submitted
21 Mar 2003
Accepted
01 May 2003
First published
13 May 2003

Org. Biomol. Chem., 2003,1, 2096-2102

Synthesis and antiviral evaluation of 2′-deoxy-2′-C-trifluoromethyl β-D-ribonucleoside analogues bearing the five naturally occurring nucleic acid bases

F. Jeannot, G. Gosselin and C. Mathé, Org. Biomol. Chem., 2003, 1, 2096 DOI: 10.1039/B303093H

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