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

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Дата последнего поиска статьи во внешних источниках: 22 марта 2016 г.

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[1] Synthesis, isomerization and biological activity of novel 2-selenohydantoin derivatives / Y. A. Ivanenkov, M. S. Veselov, I. G. Rezekin et al. // Bioorganic and Medicinal Chemistry. — 2016. — Vol. 24, no. 4. — P. 802–811. 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. [ DOI ]

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