신규 피리미딘 티오에피오 뉴크레오사이드의 합성 및 항바이러스 약효검색

Synthesis and Antiviral Evaluation of Novel Pyrimidine Thioapionucleosides

Novel 4'-hydroxymethyl blanched thioapiosyl nucleosides were synthesized in this study. The introduction of hydroxymethyl group in the 4'-position was accomplished by a 〔3,3〕-sigmatropic rearrangement. Thisoapiosyl sugar moiety was comstructed by sequential ozonolysis, reduction and cyclization. The pyrimidine nucleosidic bases (uracil, 5-fluorouracil, 5-iodouracil, 5-cchlorouracil, 5-bromouracil) were efficiently coupled by Vorbruggen glycosyl condensation procedure (per- silyated base and TMSOTf). The antiviral activities of the synthesized compounds were evaluated against the HIV-1, HSV-1, HSV-2 and EMCV. 5-lodouracil 18 showed weak antiviral activity against HSZ-1 (EC50=30.7 ㎛).