Synthesis and antiviral evaluation of 4'-C-azidomethyl-beta-D-ribofuranosyl purine and pyrimidine nucleosides.
In the search for inhibitors of the replication of RNA viruses, including hepatitis C virus (HCV), the hitherto unknown 4'-C-azidomethyl-beta-D-ribofuranosyl nucleosides of the five naturally occurring nucleic acid bases have been synthesized and their antiviral properties examined. These 4'-C-branched nucleosides were stereospecifically prepared by glycosylation of purine and pyrimidine aglycons with a suitable peracylated 4-C-azidomethyl-D-pentofuranose sugar, followed by removal of the protecting groups. The prepared compounds were tested for their activity against several viruses, but they did not show an antiviral effect.
Griffon
Jean-Francois
JF
Idenix Pharmaceuticals, Medicinal Chemistry Laboratory, Montpellier, France.
Dumas
Audrey
A
Storer
Richard
R
Sommadossi
Jean-Pierre
JP
Gosselin
Gilles
G
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011684:Purine Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D012328:RNA Viruses / Q000187:drug effects*
D000998:Antiviral Agents; D011684:Purine Nucleosides; D011741:Pyrimidine Nucleosides