Synthesis and antiviral evaluation of novel 4'-hydroxymethyl branched thioapiosyl nucleosides.
In this study, we synthesized novel 4'-hydroxymethyl branched thioapiosyl nucleosides. The thioapiosyl sugar moiety was constructed using sequential ozonolysis and reduction. The natural bases (uracil, thymine, cytosine, and adenine) were efficiently coupled using the Vorbrüggen 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 19 showed moderate anti-HIV activity (EC(50) = 19.3 microg/mL) without exhibiting any cytotoxicity up to 100 microM.
Kim
Jin Woo
JW
College of Pharmacy, Chosun University, Kwangju, Republic of Korea.
Hong
Joon Hee
JH
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D015497:HIV-1 / Q000187:drug effects; D018259:Herpesvirus 1, Human / Q000187:drug effects; D018258:Herpesvirus 2, Human / Q000187:drug effects; D006801:Humans; D008826:Microbial Sensitivity Tests; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D010084:Oxidation-Reduction
D000998:Antiviral Agents; D009705:Nucleosides