2-Substituted quinazolines: Partial agonistic and antagonistic ligands of the constitutive androstane receptor (CAR).


Journal

European journal of medicinal chemistry
ISSN: 1768-3254
Titre abrégé: Eur J Med Chem
Pays: France
ID NLM: 0420510

Informations de publication

Date de publication:
05 Nov 2023
Historique:
received: 18 05 2023
revised: 05 07 2023
accepted: 07 07 2023
medline: 22 8 2023
pubmed: 21 7 2023
entrez: 20 7 2023
Statut: ppublish

Résumé

Following the discovery of 2-(3-methoxyphenyl)-3,4-dihydroquinazoline-4-one and 2-(3-methoxyphenyl)quinazoline-4-thione as potent, but non-specific activators of the human Constitutive Androstane Receptor (CAR, NR1I3), a series of quinazolinones substituted at the C2 phenyl ring was prepared to examine their ability to selectively modulate human CAR activity. Employing cellular and in vitro TR-FRET assays with wild-type CAR or its variant 3 (CAR3) ligand binding domains (LBD), several novel partial human CAR agonists and antagonists were identified. 2-(3-Methylphenyl) quinazolinone derivatives 7d and 8d acted as partial agonists with the recombinant CAR LBD, the former in nanomolar units (EC

Identifiants

pubmed: 37473690
pii: S0223-5234(23)00597-4
doi: 10.1016/j.ejmech.2023.115631
pii:
doi:

Substances chimiques

Constitutive Androstane Receptor 0
Receptors, Cytoplasmic and Nuclear 0
Ligands 0
Quinazolines 0
Thiones 0
Receptors, Steroid 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

115631

Informations de copyright

Copyright © 2023 Elsevier Masson SAS. All rights reserved.

Déclaration de conflit d'intérêts

Declaration of competing interest The authors declare the following financial interests/personal relationships which may be considered as potential competing interests: Petr Pavek reports financial support was provided by Czech Science Foundation. Milan Pour reports financial support was provided by Charles University. Petr Pavek reports financial support was provided by Charles University. Petr Pavek reports financial support was provided by Ministry of Education Youth and Sports of the Czech Republic.

Auteurs

Zuzana Rania Brožová (ZR)

Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.

Jan Dušek (J)

Department of Pharmacology and Toxicology, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic; Department of Physiology, Faculty of Medicine in Hradec Králové, Charles University, Šimkova 870, 500 03, Hradec Králové, Czech Republic.

Norbert Palša (N)

Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.

Jana Maixnerová (J)

Department of Pharmacology and Toxicology, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.

Rajamanikkam Kamaraj (R)

Department of Pharmacology and Toxicology, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.

Lucie Smutná (L)

Department of Pharmacology and Toxicology, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.

Petr Matouš (P)

Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.

Albert Braeuning (A)

Department of Food Safety, German Federal Institute for Risk Assessment, Max-Dohrn-Str. 8-10, 10589, Berlin, Germany.

Petr Pávek (P)

Department of Pharmacology and Toxicology, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.

Jiří Kuneš (J)

Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.

Nicholas Gathergood (N)

School of Chemistry, University of Lincoln, Joseph Banks Laboratories, Green Lane, Lincoln, Lincolnshire, LN6 7DL, United Kingdom.

Marcel Špulák (M)

Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.

Milan Pour (M)

Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic. Electronic address: pour@faf.cuni.cz.

Alejandro Carazo (A)

Department of Pharmacology and Toxicology, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic. Electronic address: carazofa@faf.cuni.cz.

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