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Synthesis and biological activity of 5-aryliden-2-thiohydantoin S-aryl derivatives.
Finko, Alexander V; Skvortsov, Dmitry A; Laikov, Dimitri N; Averochkin, Gleb M; Dlin, Egor A; Kalinina, Marina A; Aladinskiy, Vladimir A; Vorobyeva, Nataliya S; Mironov, Andrei V; Beloglazkina, Elena K; Zyk, Nikolay V; Ivanenkov, Yan A; Majouga, Alexander G.
Affiliation
  • Finko AV; Department of Chemistry, Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia. Electronic address: finko.alexander@gmail.com.
  • Skvortsov DA; Department of Chemistry, Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia; Faculty of Biology and Biotechnologies, Higher School of Economics, Myasnitskaya 13, 101000 Moscow, Russia. Electronic address: skvorratd@mail.ru.
  • Laikov DN; Department of Chemistry, Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia.
  • Averochkin GM; Department of Chemistry, Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia.
  • Dlin EA; Department of Chemistry, Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia.
  • Kalinina MA; Skolkovo Institute of Science and Technology, 4 Alfred Nobel Street, 143025 Skolkovo, Russia.
  • Aladinskiy VA; Laboratory of Medical Chemistry and Bioinformatics, Moscow Institute of Physics and Technology, Institutsky Pereulok 9, 141701 Dolgoprudny, Russia.
  • Vorobyeva NS; National Research Center «Kurchatov Institute¼, Akademika Kurchatova pl. 1, 123182 Moscow, Russia.
  • Mironov AV; Department of Chemistry, Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia.
  • Beloglazkina EK; Department of Chemistry, Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia.
  • Zyk NV; Department of Chemistry, Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia.
  • Ivanenkov YA; Department of Chemistry, Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia; Laboratory of Medical Chemistry and Bioinformatics, Moscow Institute of Physics and Technology, Institutsky Pereulok 9, 141701 Dolgoprudny, Russia.
  • Majouga AG; Department of Chemistry, Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia; Skolkovo Institute of Science and Technology, 4 Alfred Nobel Street, 143025 Skolkovo, Russia; Chemistry Department. Dmitry Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, 125047 Mosco
Bioorg Chem ; 100: 103900, 2020 07.
Article in En | MEDLINE | ID: mdl-32428745
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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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Thiohydantoins / Androgens / Antineoplastic Agents Limits: Humans Language: En Journal: Bioorg Chem Year: 2020 Document type: Article
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Thiohydantoins / Androgens / Antineoplastic Agents Limits: Humans Language: En Journal: Bioorg Chem Year: 2020 Document type: Article