Synthesis of the first example of a nucleoside analogue bearing a 5'-deoxy-beta-D-allo-septanose as a seven-membered ring sugar moiety.
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.
Sizun
Gwenaëlle
G
Idenix Pharmaceuticals, Medicinal Chemistry Laboratory, Montpellier, France.
Dukhan
David
D
Griffon
Jean-François
JF
Griffe
Ludovic
L
Meillon
Jean-Christophe
JC
Leroy
Frédéric
F
Storer
Richard
R
Sommadossi
Jean-Pierre
JP
Gosselin
Gilles
G
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
D000998:Antiviral Agents; D009705:Nucleosides; D009844:Oligosaccharides