Abstract - Novel 4'-hydroxymethyl branched thioapiosyl nucleosides were synthesized in this study. The introduction of hydroxymethyl group in the 4'-position was accomplished by a [3,3]-sigmatropic rearrangement.
Thioapiosyl sugar moiety was construct...
Abstract - Novel 4'-hydroxymethyl branched thioapiosyl nucleosides were synthesized in this study. The introduction of hydroxymethyl group in the 4'-position was accomplished by a [3,3]-sigmatropic rearrangement.
Thioapiosyl sugar moiety was constructed by sequential ozonolysis, reduc- tion and cyclization. The pyrimidine nucleosidic bases (uracil, 5-fluorourac- il, 5-iodouracil, 5-chlorouracil, 5-bromouracil) were efficiently coupled by Vorbruggen 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 EMCV. 5-Iodouracil 18 showed weak antiviral activity against HSV-1 (EC50 = 30.7 μM).