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Oxazolinyl derivatives of [17(20)E]-21-norpregnene differing in the structure of A and B rings. Facile synthesis and inhibition of CYP17A1 catalytic activityстатья
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: 27 ноября 2016 г.
- Авторы: Kostin Vladimir A., Zolottsev Vladimir A., Kuzikov Alexey V., Masamrekh Rami A., Shumyantseva Victoria V., Veselovsky Alexander V., Stulov Sergey V., Novikov Roman A., Timofeev Vladimir P., Misharin Alexander Y.
- Журнал: Steroids
- Том: 115
- Год издания: 2016
- Издательство: Elsevier BV
- Местоположение издательства: Netherlands
- Первая страница: 114
- Последняя страница: 122
- DOI: 10.1016/j.steroids.2016.06.002
- Аннотация: Abstract Five 4,5-dihydro-1,3-oxazole derivatives of [17(20)E]-21-norpregnene, comprising 3β-hydroxy-5-ene (1), 3,6-dioxo-4-ene (2), 3-oxo-4-ene (3), 3α,5α-cyclo-6-oxo (4), 3β-hydroxy-6-oxo (5) fragments were synthesized. Synthesis was conducted with improved procedure, based on reaction of suitably protected [17(20)E]-pregnen-21-oic acids with ethanolamine in presence of triphenyl phosphine, carbon tetrachloride, and triethyl amine. Potency of the compounds 1–5 to inhibit 17α-hydroxylase/17,20-lyase (CYP17A1) activity was studied by highly sensitive electrochemical method, using the enzyme immobilization technique. Compounds 1 and 3 were found to be potent CYP17A1 inhibitors, compounds 2 and 5 were not active, compound 4 strongly and irreversibly suppressed the enzyme activity. Molecular docking of compounds 1–5 in the active site of CYP17A1 showed that positions of all compounds in the enzyme active site were similar.
- Добавил в систему: Кузиков Алексей Владимирович