کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1358219 981324 2016 10 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis, isomerization and biological activity of novel 2-selenohydantoin derivatives
ترجمه فارسی عنوان
سنتز، ایزومریزاسیون و فعالیت بیولوژیکی مشتقات جدید 2-سلنوهیدانتوئین
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
چکیده انگلیسی

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.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Bioorganic & Medicinal Chemistry - Volume 24, Issue 4, 15 February 2016, Pages 802–811
نویسندگان
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