Simple synthesis and anti-HIV activity of novel 3'-vinyl branched apiosyl pyrimidine nucleosides.
Novel vinyl branched apiosyl nucleosides were synthesized in this study. Apiosyl sugar moiety was constructed by sequential ozonolysis and reductions. The bases (uracil and thymine) were efficiently coupled by glycosyl condensation procedure (persilyated base and TMSOTf). The antiviral activities of the synthesized compounds were evaluated against the HIV-1, HSV-1, HSV-2, and HCMV. Compound 10beta displayed moderate anti-HIV activity (EC50 = 17.3 microg/mL) without exhibiting any cytotoxicity up to 100 microM.
Oh
Chang Hyun
CH
Medicinal Chemistry Research Center, Korea Institute of Science and Technology, Seoul, Republic of Korea.
Kim
Jin Woo
JW
Hong
Joon Hee
JH
D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006678:HIV / Q000187:drug effects; D010429:Pentoses / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D014780:Viruses / Q000187:drug effects
C514092:1-(hydroxymethyl-4-vinyltetrahydrofuran-2-yl)uracil; D019380:Anti-HIV Agents; D010429:Pentoses; D011741:Pyrimidine Nucleosides; D014753:Vinyl Compounds; C004983:apiose; D014529:Uridine