title: Synthesis of the first example of a nucleoside analogue bearing a 5'-deoxy-beta-D-allo-septanose as a seven-membered ring sugar moiety.
abstract: The first example of a nucleoside analogue bearing a 5'-deoxy-beta-D-allo-septanose as a seven-membered ring sugar moiety, namely 9-(5-deoxy-beta-D-allo-septanosyl)-adenine, is reported. This compound was synthesized in 14 steps from the commercially available D-glycero-D-gulo-1,4-lactone. When evaluated in cell culture experiments against a broad range of viruses, it did not exhibit any significant antiviral effect or cytotoxicity.
authors.affiliation: Idenix Pharmaceuticals, Medicinal Chemistry Laboratory, Montpellier, France.
authors.forename: Gwenaëlle
authors.initials: G
authors.lastname: Sizun
authors.forename: David
authors.initials: D
authors.lastname: Dukhan
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Griffon
authors.forename: Ludovic
authors.initials: L
authors.lastname: Griffe
authors.forename: Jean-Christophe
authors.initials: JC
authors.lastname: Meillon
authors.forename: Frédéric
authors.initials: F
authors.lastname: Leroy
authors.forename: Richard
authors.initials: R
authors.lastname: Storer
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Sommadossi
authors.forename: Gilles
authors.initials: G
authors.lastname: Gosselin
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005416:Flavivirus / Q000187:drug effects; D016174:Hepacivirus / Q000187:drug effects; D008956:Models, Chemical; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D010576:Pestivirus / Q000187:drug effects
chemical_list: D000998:Antiviral Agents; D009705:Nucleosides; D009844:Oligosaccharides