Bioorganic Chemistry, volume 100, pages 103900

Synthesis and biological activity of 5-aryliden-2-thiohydantoin S-aryl derivatives

Finko A V 1
Ivanenkov Yan 2, 3
Beloglazkina Elena K
Skvortsov Dmitry A.
Averochkin Gleb M
Dlin Egor A 1
Zyk Nikolay V. 1
Vorobyeva Nataliya S 4
Aladinskiy Vladimir A.
Kalinina Marina A
Mironov Andrei V. 1
Skvortsov Dmitry 3, 5
Averochkin Gleb M 1
A. Aladinskiy Vladimir 7
Publication typeJournal Article
Publication date2020-07-01
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor5.1
ISSN00452068, 10902120
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Abstract
Three new and complementary approaches to S-arylation of 2-thiohydantoins have been developed: copper-catalyzed cross coupling with either arylboronic acids or aryl iodides under mild conditions, or direct nucleophilic substitution in activated aryl halides. For 38 diverse compounds, reaction yields for all three methods have been determined. Selected by molecular docking, they have been tested on androgen receptor activation, and p53-Mdm2 regulation, and A549, MCF7, VA13, HEK293T, PC3, LnCAP cell lines for cytotoxicity, Two of them turned out to be promising as androgen receptor activators (likely by allosteric regulation), and another one is shown to activate the p53 cascade. It is hoped that 2-thiohydantoin S-arylidenes are worth further studies as biologically active compounds.

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Finko A. V. et al. Synthesis and biological activity of 5-aryliden-2-thiohydantoin S-aryl derivatives // Bioorganic Chemistry. 2020. Vol. 100. p. 103900.
GOST all authors (up to 50) Copy
Skvortsov D. A., Majouga A. G., Ivanenkov Y., Zyk N. V., Beloglazkina E. K., Mironov A. V., Vorobyeva N. S., Aladinskiy V. A., Kalinina M. A., Dlin E. A., Averochkin G. M., Laikov D., Finko A. V., Skvortsov D., Averochkin G. M., Kalinina M. A., A. Aladinskiy V., Beloglazkina E. K. Synthesis and biological activity of 5-aryliden-2-thiohydantoin S-aryl derivatives // Bioorganic Chemistry. 2020. Vol. 100. p. 103900.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1016/j.bioorg.2020.103900
UR - https://doi.org/10.1016%2Fj.bioorg.2020.103900
TI - Synthesis and biological activity of 5-aryliden-2-thiohydantoin S-aryl derivatives
T2 - Bioorganic Chemistry
AU - Finko, A V
AU - Skvortsov, Dmitry A.
AU - Laikov, Dimitri
AU - Averochkin, Gleb M
AU - Dlin, Egor A
AU - Kalinina, Marina A
AU - Aladinskiy, Vladimir A.
AU - Vorobyeva, Nataliya S
AU - Mironov, Andrei V.
AU - Beloglazkina, Elena K
AU - Zyk, Nikolay V.
AU - Ivanenkov, Yan
AU - Majouga, Alexander G.
AU - Skvortsov, Dmitry
AU - Averochkin, Gleb M
AU - Kalinina, Marina A
AU - A. Aladinskiy, Vladimir
AU - Beloglazkina, Elena K.
PY - 2020
DA - 2020/07/01 00:00:00
PB - Elsevier
SP - 103900
VL - 100
SN - 0045-2068
SN - 1090-2120
ER -
BibTex
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BibTex Copy
@article{2020_Finko
author = {A V Finko and Dmitry A. Skvortsov and Dimitri Laikov and Gleb M Averochkin and Egor A Dlin and Marina A Kalinina and Vladimir A. Aladinskiy and Nataliya S Vorobyeva and Andrei V. Mironov and Elena K Beloglazkina and Nikolay V. Zyk and Yan Ivanenkov and Alexander G. Majouga and Dmitry Skvortsov and Gleb M Averochkin and Marina A Kalinina and Vladimir A. Aladinskiy and Elena K. Beloglazkina},
title = {Synthesis and biological activity of 5-aryliden-2-thiohydantoin S-aryl derivatives},
journal = {Bioorganic Chemistry},
year = {2020},
volume = {100},
publisher = {Elsevier},
month = {jul},
url = {https://doi.org/10.1016%2Fj.bioorg.2020.103900},
pages = {103900},
doi = {10.1016/j.bioorg.2020.103900}
}
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