Abstract
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.
MeSH terms
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Anti-HIV Agents / chemical synthesis
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Anti-HIV Agents / chemistry*
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Anti-HIV Agents / pharmacology*
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HIV / drug effects
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Pentoses / chemistry
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Pyrimidine Nucleosides / chemical synthesis
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Pyrimidine Nucleosides / chemistry*
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Pyrimidine Nucleosides / pharmacology*
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Uridine / analogs & derivatives*
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Uridine / chemical synthesis
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Uridine / chemistry
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Uridine / pharmacology
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Vinyl Compounds / chemical synthesis
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Vinyl Compounds / chemistry*
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Vinyl Compounds / pharmacology*
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Viruses / drug effects
Substances
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1-(hydroxymethyl-4-vinyltetrahydrofuran-2-yl)uracil
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Anti-HIV Agents
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Pentoses
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Pyrimidine Nucleosides
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Vinyl Compounds
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apiose
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Uridine