Ullmann-type C-Se Cross-Coupling in the Hydantoin Family: Synthesis, Mechanistic Studies, and Tests of Biological Activity.

Catalysis Copper Hydantoins / pharmacology Imidazolines

Journal

The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R

Informations de publication

Date de publication:
06 03 2020
Historique:
pubmed: 17 1 2020
medline: 24 6 2021
entrez: 17 1 2020
Statut: ppublish

Résumé

An attractive strategy for C-Se bond formation by Ullmann-type copper(I)-promoted cross-coupling is developed. A wide range of aryliodides reacts with various disubstituted 2-selenohydantoins under mild conditions and provides Se-arylated imidazolines in moderate to high yields. Computational mechanistic studies show the oxidative addition/intramolecular reductive elimination likely to be the lowest-energy pathway. Cytotoxic activity of all 43 reaction products has been tested in vitro against MCF7 and A549 cancer cell lines with VA13 and MCF10a control cells.

Identifiants

DOI: 10.1021/acs.joc.9b03045 PMID: 31944122
pubmed: 31944122
doi: 10.1021/acs.joc.9b03045
doi:

Substances chimiques

Hydantoins 0
Imidazolines 0
Copper 789U1901C5

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

3160-3173

Auteurs

Oleksandr Vyhivskyi (O)

Chemistry Department, Moscow State University, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russia.

Dimitri N Laikov (DN)

Chemistry Department, Moscow State University, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russia.
ORCID: 0000-0002-2634-8780

Alexander V Finko (AV)

Chemistry Department, Moscow State University, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russia.
ORCID: 0000-0002-1334-9485

Dmitry A Skvortsov (DA)

Chemistry Department, Moscow State University, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russia.
Biology and Biotechnology Department, Higher School of Economics, Myasnitskaya 13, Moscow 101000, Russia.

Irina V Zhirkina (IV)

Chemistry Department, Moscow State University, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russia.

Victor A Tafeenko (VA)

Chemistry Department, Moscow State University, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russia.

Nikolay V Zyk (NV)

Chemistry Department, Moscow State University, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russia.

Alexander G Majouga (AG)

Chemistry Department, Moscow State University, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russia.
National University of Science and Technology, Leninskii pr., 4, Moscow 119049, Russia.
Mendeleev University of Chemical Technology, Miusskaya pl. 9, Moscow 125047, Russia.
ORCID: 0000-0002-5184-5551

Elena K Beloglazkina (EK)

Chemistry Department, Moscow State University, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russia.

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Classifications MeSH

questionsmedicales.fr › Phénomènes chimiques › Catalyse › Ullmann-type C-Se Cross-Coupling in the...
questionsmedicales.fr › Produits chimiques inorganiques › Métaux › Métaux lourds › Cuivre › Ullmann-type C-Se Cross-Coupling in the...
questionsmedicales.fr › Composés hétérocycliques › Composés hétéromonocycliques › Azoles › Imidazoles › Imidazolidines › Hydantoïnes › Ullmann-type C-Se Cross-Coupling in the...
questionsmedicales.fr › Composés hétérocycliques › Composés hétéromonocycliques › Azoles › Imidazoles › Imidazolines › Ullmann-type C-Se Cross-Coupling in the...