Synthesis, isomerization and biological activity of novel 2-selenohydantoin derivatives

Ivanenkov, Y.A.; Veselov, M.S.; Rezekin, I.G.; Skvortsov, D.A.; Sandulenko, Y.B.; Polyakova, M.V.; Bezrukov, D.S.; Vasilevsky, S.V.; Kukushkin, M.E.; Moiseeva, A.A.; Finko, A.V.; Koteliansky, V.E.; Klyachko, N.L.; Filatova, L.A.; Beloglazkina, E.K.; Zyk, N.V.; Majouga, A.G.

Авторы: Ivanenkov Yan A., Veselov Mark S., Rezekin Igor G., Skvortsov Dmitriy A., Sandulenko Yuri B., Polyakova Marina V., Bezrukov Dmitry S., Vasilevsky Sergey V., Kukushkin Maxim E., Moiseeva Anna A., Finko Alexander V., Koteliansky Victor E., Klyachko Natalia L., Filatova Lubov A., Beloglazkina Elena K., Zyk Nikolay V., Majouga Alexander G.
Журнал: Bioorganic and Medicinal Chemistry
Том: 24
Номер: 4
Год издания: 2016
Издательство: Pergamon Press Ltd.
Местоположение издательства: United Kingdom
Первая страница: 802
Последняя страница: 811
DOI: 10.1016/j.bmc.2015.12.050
Аннотация: A set of novel selenohydantoins were synthesized via a convenient and versatile approach involving the reaction of isoselenocyanates with various amines. We also revealed an unexpected Z→E isomerization of pyridin-2-yl-substituted selenohydantoins in the presence of Cu2+ cations. The detailed mechanism of this transformation was suggested on the basis of quantum-chemical calculations, and the key role of Cu2+ was elucidated. The obtained compounds were subsequently evaluated against a panel of different cancer cell lines. As a result, several molecules were identified as promising micromolar hits with good selectivity index. Instead of analogous thiohydantoins, which have been synthesized previously, selenohydantoins demonstrated a relatively high antioxidant activity comparable (or greater) to the reference molecule, Ebselen, a clinically approved drug candidate. The most active compounds have been selected for further biological trials.
Добавил в систему: Белоглазкина Елена Кимовна

	ИСТИНА	Войти в систему Регистрация
	ИПМех РАН
	Главная Поиск Статистика О проекте Помощь

ИСТИНА

ИПМех РАН

Synthesis, isomerization and biological activity of novel 2-selenohydantoin derivativesстатья