Impact of hydroxy moieties at the benzo[7]annulene ring system of GluN2B ligands: Design, synthesis and biological evaluation.
Cytoprotective activity
Docking studies
GluN2B selective antagonists
Ifenprodil binding site
Metabolic stability
NMDA receptor
Negative allosteric modulators
Selectivity
Structure-activity relationships
Structure-affinity relationships
Journal
Bioorganic & medicinal chemistry
ISSN: 1464-3391
Titre abrégé: Bioorg Med Chem
Pays: England
ID NLM: 9413298
Informations de publication
Date de publication:
01 12 2019
01 12 2019
Historique:
received:
29
07
2019
revised:
25
09
2019
accepted:
28
09
2019
pubmed:
28
10
2019
medline:
25
9
2020
entrez:
26
10
2019
Statut:
ppublish
Résumé
In this study, the impact of one or two hydroxy moieties at the benzo[7]annulene scaffold on the GluN2B affinity and cytoprotective activity was analyzed. The key intermediate for the synthesis of OH-substituted benzo[7]annulenamines 11-13 and 17 was the epoxyketone 8. Reductive epoxide opening of 8 resulted with high regioselectivity in the 5-hydroxyketone 9 (Pd(OAc)
Identifiants
pubmed: 31648876
pii: S0968-0896(19)31300-8
doi: 10.1016/j.bmc.2019.115146
pii:
doi:
Substances chimiques
Bridged Bicyclo Compounds
0
Ligands
0
NR2B NMDA receptor
0
Receptors, N-Methyl-D-Aspartate
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
115146Informations de copyright
Copyright © 2019 Elsevier Ltd. All rights reserved.