One-pot four-component synthesis of thiazolidin-2-imines using Cu
Acetylcholinesterase
/ chemistry
Binding Sites
Catalysis
Cholinesterase Inhibitors
/ chemical synthesis
Copper
/ chemistry
Humans
Imines
/ chemistry
Inhibitory Concentration 50
Molecular Conformation
Molecular Docking Simulation
Structure-Activity Relationship
Thermodynamics
Thiazoles
/ chemistry
Zinc
/ chemistry
Cholinesterase inhibitors
Cooperative catalysis
Molecular docking
One-pot four-component reaction
Thiazolidine-2-imines
Journal
Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703
Informations de publication
Date de publication:
03 2019
03 2019
Historique:
received:
11
10
2018
revised:
23
11
2018
accepted:
03
12
2018
pubmed:
6
1
2019
medline:
14
1
2020
entrez:
6
1
2019
Statut:
ppublish
Résumé
An efficient one-pot four-component strategy involving aldehydes, amines, alkynes and isothiocyanates has been developed to access a novel series of thiazolidine-2-imines (5a-x). This process operates under the action of a cooperative catalysis composed of Cu(I) and Zn(II) delivering the desired five-membered heterocyclic compounds in good to excellent yields. Notably, this transformation avoids the use of pre-formed imines or propargylamines and proceeds via an intramolecular 5-exo-dig hydrothiolation reaction of the in situ formed propargyl thiourea. Furthermore, the biological application of these motifs was demonstrated in terms of their strong acetylcholinesterase (AChE) inhibitory activity where compound 5s was identified as the lead AChE inhibitor with an IC
Identifiants
pubmed: 30610971
pii: S0045-2068(18)31154-4
doi: 10.1016/j.bioorg.2018.12.002
pii:
doi:
Substances chimiques
Cholinesterase Inhibitors
0
Imines
0
Thiazoles
0
Copper
789U1901C5
Acetylcholinesterase
EC 3.1.1.7
Zinc
J41CSQ7QDS
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
518-528Informations de copyright
Copyright © 2018 Elsevier Inc. All rights reserved.