title: Enantiomeric 2',3'-dideoxycytidine derivatives are potent human immunodeficiency virus inhibitors in cell cultures.
abstract: 2',3'-dideoxy-beta-L-cytidine (beta-L-DDC) and its 5-fluoro derivative (beta-L-5-F-DDC) have been stereospecifically synthesized by a multi-step reaction sequence from L-xylose and their anti-HIV properties examined. Among these two L-enantiomers, the hitherto unknown beta-L-5-F-DDC emerged as a potent anti-HIV-1 and HIV-2 compound in different cell culture systems, with selectivity indices similar or superior to those of the currently licensed drug DDC which has the natural beta-D configuration.
authors.affiliation: Laboratoire de Chimie Bioorganique, URA CNRS 488, Université de Montpellier-II, Sciences et Techniques du Languedoc, Montpellier, France.
authors.forename: G
authors.initials: G
authors.lastname: Gosselin
authors.forename: C
authors.initials: C
authors.lastname: Mathé
authors.forename: M C
authors.initials: MC
authors.lastname: Bergogne
authors.forename: A M
authors.initials: AM
authors.lastname: Aubertin
authors.forename: A
authors.initials: A
authors.lastname: Kirn
authors.forename: R F
authors.initials: RF
authors.lastname: Schinazi
authors.forename: J P
authors.initials: JP
authors.lastname: Sommadossi
authors.forename: J L
authors.initials: JL
authors.lastname: Imbach
mesh_terms: D002478:Cells, Cultured; D006678:HIV / Q000187:drug effects* / Q000254:growth & development; D015497:HIV-1 / Q000187:drug effects; D015498:HIV-2 / Q000187:drug effects; D008968:Molecular Conformation; D013237:Stereoisomerism; D016047:Zalcitabine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: C085719:2',3'-dideoxy-beta-5-fluorocytidine; D016047:Zalcitabine