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Synthesis and biological properties of pyrimidine 4′-fluoronucleosides and 4′-fluorouridine 5′-O-triphosphateстатья
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 11 декабря 2015 г.
- Авторы: Ivanov M.A., Ludva G.S., Mukovnya A.V., Kochetkov S.N., Tunitskaya V.L., Alexandrova L.A.
- Журнал: Russian Journal of Bioorganic Chemistry
- Том: 36
- Номер: 4
- Год издания: 2010
- Издательство: Maik Nauka/Interperiodica Publishing
- Местоположение издательства: Russian Federation
- Первая страница: 488
- Последняя страница: 496
- DOI: 10.1134/s1068162010040072
- Аннотация: 4'-Fluoro-2',3'-O-isopropylidenecytidine was synthesized by the treatment of 5'-O-acetyl-4'-fluoro-2',3'-O-isopropylideneuridine with triazole and 4-chlorophenyl dichlorophosphate followed by ammonolysis. The interaction of 4'-fluoro-2',3'-O-isopropylidenecytidine with hydroxylamine resulted in 4'-fluoro-2',3'-O-isopropylidene-5'-O-acetyl-N (4)-hydroxycytidine. The removal of the 2',3'-O-isopropylidene groups led to acetyl derivatives of 4'-fluorouridine, 4'-fluorocytidine, and 4'-fluoro-N (4)-hydroxycytidine. 4'-Fluorouridine 5'-O-triphosphate was obtained in three steps starting from 4'-fluoro-2',3'-O-isopropylideneuridine. 4'-Fluorouridine 5'-O-triphosphate was shown to be an effective inhibitor of HCV RNA-dependent RNA polymerase and a substrate for the NTPase reaction catalyzed by the HCV NS3 protein, the hydrolysis rate being similar to that of ATP. It could also activate a helicase reaction with an efficacy of only threefold lower than that for ATP.
- Добавил в систему: Кочетков Сергей Николаевич