Bioorganic and Medicinal Chemistry, volume 24, issue 4, pages 802-811

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

Ivanenkov Yan 1, 2, 3
Veselov Mark S. 4
Rezekin Igor G 4
Sandulenko Yuri B. 4
Polyakova Marina V 4
Bezrukov Dmitry S. 1
Vasilevsky Sergey V 1
Kukushkin Maxim E. 1
Finko A V 1
Koteliansky Victor E. 1
Filatova Lubov A 1
Zyk Nikolay V. 1
Publication typeJournal Article
Publication date2016-02-01
Quartile SCImago
Q2
Quartile WOS
Q1
Impact factor3.5
ISSN09680896, 14643391
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Pharmaceutical Science
Clinical Biochemistry
Molecular Medicine
Abstract
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 Cu(2+) cations. The detailed mechanism of this transformation was suggested on the basis of quantum-chemical calculations, and the key role of Cu(2+) 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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Ivanenkov Y. et al. Synthesis, isomerization and biological activity of novel 2-selenohydantoin derivatives // Bioorganic and Medicinal Chemistry. 2016. Vol. 24. No. 4. pp. 802-811.
GOST all authors (up to 50) Copy
Ivanenkov Y., Veselov M. S., Rezekin I. G., Skvortsov D., 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. Synthesis, isomerization and biological activity of novel 2-selenohydantoin derivatives // Bioorganic and Medicinal Chemistry. 2016. Vol. 24. No. 4. pp. 802-811.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1016/j.bmc.2015.12.050
UR - https://doi.org/10.1016%2Fj.bmc.2015.12.050
TI - Synthesis, isomerization and biological activity of novel 2-selenohydantoin derivatives
T2 - Bioorganic and Medicinal Chemistry
AU - Ivanenkov, Yan
AU - Veselov, Mark S.
AU - Rezekin, Igor G
AU - Sandulenko, Yuri B.
AU - Polyakova, Marina V
AU - Vasilevsky, Sergey V
AU - Kukushkin, Maxim E.
AU - Moiseeva, Anna A.
AU - Finko, A V
AU - Koteliansky, Victor E.
AU - Filatova, Lubov A
AU - Zyk, Nikolay V.
AU - Skvortsov, Dmitry
AU - Bezrukov, Dmitry S.
AU - Klyachko, Natalia L.
AU - Beloglazkina, Elena K.
AU - Majouga, Alexander G.
PY - 2016
DA - 2016/02/01 00:00:00
PB - Elsevier
SP - 802-811
IS - 4
VL - 24
SN - 0968-0896
SN - 1464-3391
ER -
BibTex |
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BibTex Copy
@article{2016_Ivanenkov
author = {Yan Ivanenkov and Mark S. Veselov and Igor G Rezekin and Yuri B. Sandulenko and Marina V Polyakova and Sergey V Vasilevsky and Maxim E. Kukushkin and Anna A. Moiseeva and A V Finko and Victor E. Koteliansky and Lubov A Filatova and Nikolay V. Zyk and Dmitry Skvortsov and Dmitry S. Bezrukov and Natalia L. Klyachko and Elena K. Beloglazkina and Alexander G. Majouga},
title = {Synthesis, isomerization and biological activity of novel 2-selenohydantoin derivatives},
journal = {Bioorganic and Medicinal Chemistry},
year = {2016},
volume = {24},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016%2Fj.bmc.2015.12.050},
number = {4},
pages = {802--811},
doi = {10.1016/j.bmc.2015.12.050}
}
MLA
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MLA Copy
Ivanenkov, Yan, et al. “Synthesis, isomerization and biological activity of novel 2-selenohydantoin derivatives.” Bioorganic and Medicinal Chemistry, vol. 24, no. 4, Feb. 2016, pp. 802-811. https://doi.org/10.1016%2Fj.bmc.2015.12.050.
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