Synthesis and antiviral evaluation of novel 4'-hydroxymethyl branched apiosyl nucleosides.
Novel 4'-hydroxymethyl branched apiosyl nucleosides were synthesized in this study. The introduction of a hydroxymethyl group in the 4'-position was accomplished by a [3,3]-sigmatropic rearrangement. Apiosyl sugar moiety was constructed by sequential ozonolysis and reductions. The natural bases (uracil, thymine, cytosine, and adenine) were efficiently coupled by a classical glycosyl condensation procedure (persilyated base and TMSOTf). The antiviral activities of the synthesized compounds were evaluated against HIV-1, HSV-1, HSV-2, and HCMV. Compound 18 displayed moderate anti-HCMV activity (EC50 = 20.1 microg/mL) without exhibiting any cytotoxicity up to 100 microM.
Kim
Jin Woo
JW
College of Pharmacy, Chosun University, Kwangju 501-759, Republic of Korea.
Hong
Joon Hee
JH
D000085:Acetates / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D003587:Cytomegalovirus / Q000187:drug effects; D015497:HIV-1 / Q000187:drug effects; D006900:Hydroxylation; D008745:Methylation; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D018139:Simplexvirus / Q000187:drug effects
D000085:Acetates; D000998:Antiviral Agents; D009705:Nucleosides