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Synthesis and Antiviral Evaluation of Novel Pyrimidine Thioapionucleosides  

Lee Rae-Sang (College of Pharmacy, Chosun University)
Hong Joon-Hee (College of Pharmacy, Chosun University)
Ko Ok-Hyun (College of Pharmacy, Chosun University)
Publication Information
YAKHAK HOEJI / v.50, no.2, 2006 , pp. 65-69 More about this Journal
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, reduction and cyclization. The pyrimidine nucleosidic bases (uracil, 5-fluorouracil, 5-iodouracil, 5-chlorouracil, 5-bromouracil) were efficiently coupled by Vorbruggen glycosyl condensation procedure (per-silyated base and TMSOTf). The antiviral activities of the synthesised compounds were evaluated against the HIV-1, HSV-1, HSV-2 and EMCV 5-Iodouracil 18 showed weak antiviral activity against HSV-1 $(EC_{50}=30.7{\mu}M)$.
Keywords
antiviral agent; thioapionucleoside; Vorbruggen reaction;
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