Evaluating the effects of fluorine on biological properties and metabolic stability of some antitubulin 3-substituted 7-phenyl-pyrroloquinolinones.
Antineoplastic Agents
/ chemical synthesis
Cell Line
Cell Proliferation
/ drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Fluorine
/ chemistry
Humans
Microsomes, Liver
/ drug effects
Models, Molecular
Molecular Structure
Quinolones
/ chemistry
Structure-Activity Relationship
Tubulin Modulators
/ chemistry
Anti-tubulin
Apoptosis
Fluoro-phenylpyrroloquinolinone
Metabolic stability
Molecular docking
Structure-activity relationships
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:
15 Sep 2019
15 Sep 2019
Historique:
received:
28
03
2019
revised:
31
05
2019
accepted:
31
05
2019
pubmed:
14
6
2019
medline:
3
10
2019
entrez:
14
6
2019
Statut:
ppublish
Résumé
A small number of fluorinated 7-phenyl-pyrroloquinolinone (7-PPyQ) derivatives was synthesized in an attempt to improve the metabolic stability of 3N-ethyl-7-PPyQ and 3N-benzoyl-7-PPyQ. The possible impacts of the fluorine-hydrogen isosterism on both biological activity and metabolic stability were evaluated. Introduction of a fluorine atom in the 2 or 3 position of the 7-phenyl ring yielded the 7-PPyQ derivatives 12, 13 and 15, which showed potent cytotoxicity (low micromolar and sub-nanomolar GI
Identifiants
pubmed: 31195171
pii: S0223-5234(19)30516-1
doi: 10.1016/j.ejmech.2019.05.092
pii:
doi:
Substances chimiques
Antineoplastic Agents
0
Quinolones
0
Tubulin Modulators
0
Fluorine
284SYP0193
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
297-314Informations de copyright
Copyright © 2019 Elsevier Masson SAS. All rights reserved.