title: Synthesis and antiviral evaluation of 2'-deoxy-2'-C-trifiuoromethyl beta-D-ribonucleoside analogues bearing the five naturally occurring nucleic acid bases.
abstract: 2'-Deoxy-2'-C-trifluoromethyl-beta-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 beta-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.
authors.affiliation: Laboratoire de Chimie Organique Biomoléculaire de Synthèse, UMR 5625 CNRS-Université Montpellier II, case courrier 008, Place Eugene Bataillon, 34095 Montpellier Cedex 5, France.
authors.forename: Frédéric
authors.initials: F
authors.lastname: Jeannot
authors.forename: Gilles
authors.initials: G
authors.lastname: Gosselin
authors.forename: Christophe
authors.initials: C
authors.lastname: Mathé
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003853:Deoxyribonucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D006031:Glycosylation; D006678:HIV / Q000187:drug effects; D006515:Hepatitis B virus / Q000187:drug effects; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011687:Purines / Q000737:chemistry; D011743:Pyrimidines / Q000737:chemistry; D012328:RNA Viruses / Q000187:drug effects
chemical_list: D000998:Antiviral Agents; D003853:Deoxyribonucleosides; D006845:Hydrocarbons, Fluorinated; D011687:Purines; D011743:Pyrimidines