Synthesis and anti-HIV activity of 5-alkoxymethyl-3'-azido-2',3- dideoxyuridines.
Methyl 3-azido-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-erythro-furanosi de (3) was coupled with silylated 5-hydroxymethyluracil (1a) and its C1-C6 alkyl ethers 1b-g to give the corresponding protected nucleosides 4a-g which were deprotected with Bu4NF to afford 3-azido nucleosides 5a-g and 6a-g. The alpha-anomers 6f,g show moderate activity against HIV. No significant activity against HSV-1 was found for the compounds 5 and 6.
Abdel-Megied
A E
AE
Department of Chemistry, Odense University, Denmark.
Hansen
P
P
Pedersen
E B
EB
Nielsen
C
C
Nielsen
C M
CM
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects*; D006801:Humans; D018139:Simplexvirus / Q000187:drug effects; D015215:Zidovudine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology
D000998:Antiviral Agents; D015215:Zidovudine