Synthesis of novel isoflavone/benzo-δ-sultam hybrids as potential anti-inflammatory drugs.
Animals
Anti-Inflammatory Agents, Non-Steroidal
/ chemical synthesis
Cell Line
Dose-Response Relationship, Drug
Isoflavones
/ chemistry
Lipopolysaccharides
/ antagonists & inhibitors
Mice
Microglia
/ drug effects
Molecular Structure
Nitric Oxide
/ antagonists & inhibitors
Structure-Activity Relationship
Sulfonamides
/ chemistry
Tumor Necrosis Factor-alpha
/ antagonists & inhibitors
Anti-inflammatory
Isoflavone
Microglia
TNF-α
δ-sultam
Journal
Bioorganic & medicinal chemistry letters
ISSN: 1464-3405
Titre abrégé: Bioorg Med Chem Lett
Pays: England
ID NLM: 9107377
Informations de publication
Date de publication:
15 02 2021
15 02 2021
Historique:
received:
02
09
2020
revised:
15
12
2020
accepted:
20
12
2020
pubmed:
29
12
2020
medline:
23
7
2021
entrez:
28
12
2020
Statut:
ppublish
Résumé
A small series of novel isoflavone/benzo-δ-sultam hybrids was synthesised and evaluated as potential anti-inflammatory and neuroprotective drugs in LPS-activated BV2 microglia. The benzo-δ-sultam core was constructed in a two-step reaction by coupling 2-halobenzenesulfonamide derivatives with terminal alkynes, followed by a 6-endo-dig cyclisation. The synthesised compounds, including precursors and hybrids, were tested for their ability to inhibit NO and TNF-α production in LPS-stimulated BV2 microglial cells, and the results are promising. The most potent hybrid reduces the NO production to 41%, and the TNF-α to 34% at 20 µM final concentration in the well.
Identifiants
pubmed: 33359607
pii: S0960-894X(20)30872-6
doi: 10.1016/j.bmcl.2020.127761
pii:
doi:
Substances chimiques
Anti-Inflammatory Agents, Non-Steroidal
0
Isoflavones
0
Lipopolysaccharides
0
Sulfonamides
0
Tumor Necrosis Factor-alpha
0
beta-sultam
0
Nitric Oxide
31C4KY9ESH
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
127761Informations de copyright
Copyright © 2020 Elsevier Ltd. All rights reserved.