Asymmetric synthesis and biological evaluation of imidazole- and oxazole-containing synthetic lipoxin A
Anti-inflammatory effects
Asymmetric synthesis
Lipoxins
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 Jan 2019
15 Jan 2019
Historique:
received:
27
07
2018
revised:
02
10
2018
accepted:
19
10
2018
pubmed:
13
11
2018
medline:
5
2
2019
entrez:
13
11
2018
Statut:
ppublish
Résumé
Lipoxins (LXs) are endogenously generated eicosanoids with potent bio-actions consistent with attenuation of inflammation. The costly synthesis and metabolic instability of LXs may limit their therapeutic potential. Here we report the synthesis and characterization of novel imidazole-/oxazole-containing synthetic-LX-mimetics (sLXms). The key steps of asymmetric synthesis of putative sLXms include a Suzuki reaction and an asymmetric ketone reduction. The effect of the novel compounds on inflammatory responses was assessed using a human monocyte cell line stably expressing a Nuclear Factor Kappa B (NFkB) reporter gene, by investigating downstream cytokine secretion. The potential interaction of the imidazoles/oxazoles with the molecular target of LXs, i.e. G-protein coupled receptor (GPCR) Formyl Peptide Receptor 2 (ALX/FPR2) was investigated using a cell system where ALX/FPR2 is coupled to the Gα
Identifiants
pubmed: 30419493
pii: S0223-5234(18)30919-X
doi: 10.1016/j.ejmech.2018.10.049
pii:
doi:
Substances chimiques
Imidazoles
0
Lipoxins
0
NF-kappa B
0
Oxazoles
0
Receptors, Formyl Peptide
0
formyl peptide receptor 2, mouse
0
lipoxin A4
0
imidazole
7GBN705NH1
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
80-108Informations de copyright
Copyright © 2018 Elsevier Masson SAS. All rights reserved.