Synthesis and evaluation of antiviral activity of L-acosamine and L-ristosamine nucleosides of furanose configuration.
Mercuric-catalyzed hydrolysis of acetylated L-rhamnal 1 gives an alpha,beta-unsaturated aldehyde 2. 1,4-Addition of DBU-phthalimide salt with concomitant acetyl shift resulted in L-ribo and L-arabino isomers of 5-O-acetyl-2,3,6-trideoxy-3-phthalimido-hexofuranose 3 and 4. After acetylation at the anomeric center, coupling with silylated thymine resulted in three new nucleosides, with L-acosamine and L-ristosamine of furanose configuration as the carbohydrate moiety. The target compounds have been evaluated for their antiviral activity against HIV and HSV-1.
Lau
J
J
Department of Chemistry, Odense University, Denmark.
Pedersen
E B
EB
Nielsen
C M
CM
D000998:Antiviral Agents / Q000138:chemical synthesis*; D002236:Carbohydrate Conformation; D002460:Cell Line; D015497:HIV-1 / Q000187:drug effects; D006595:Hexosamines; D006801:Humans; D007202:Indicators and Reagents; D007536:Isomerism; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D018139:Simplexvirus / Q000187:drug effects
D000998:Antiviral Agents; D006595:Hexosamines; D007202:Indicators and Reagents; D009705:Nucleosides; C010783:ristosamine; C010669:acosamine