Synthesis, biological activity and molecular modeling studies on 1H-benzimidazole derivatives as acetylcholinesterase inhibitors

A series of substituted benzimidazole derivatives were synthesized and evaluated AChE/BuChE enzyme inhibitor activities. A series of N-{2-[4-(1H-benzimidazole-2-yl)phenoxy]ethyl}substituted amine derivatives were designed to assess cholinesterase inhibitor activities. Acetylcholinesterase (AChE) and...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2013-09, Vol.21 (17), p.4928-4937
Main Authors: Alpan, Ayşe Selcen, Parlar, Sülünay, Carlino, Luca, Tarikogullari, Ayse Hande, Alptüzün, Vildan, Güneş, Hasan Semih
Format: Article
Language:English
Subjects:
1H-Benzimidazole
acetylcholinesterase
Acetylcholinesterase - chemistry
Acetylcholinesterase - metabolism
Acetylcholinesterase inhibitor
Animals
Benzimidazoles - chemical synthesis
Benzimidazoles - chemistry
Benzimidazoles - metabolism
Binding Sites
bioactive properties
Butyrylcholinesterase - chemistry
Butyrylcholinesterase - metabolism
Butyrylcholinesterase inhibitor
Catalytic Domain
cholinesterase
Cholinesterase Inhibitors - chemical synthesis
Cholinesterase Inhibitors - chemistry
Cholinesterase Inhibitors - metabolism
Humans
Molecular Docking Simulation
molecular dynamics
Molecular modeling
Protein Binding
Synthesis
Torpedo - metabolism
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Summary:A series of substituted benzimidazole derivatives were synthesized and evaluated AChE/BuChE enzyme inhibitor activities. A series of N-{2-[4-(1H-benzimidazole-2-yl)phenoxy]ethyl}substituted amine derivatives were designed to assess cholinesterase inhibitor activities. Acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitor activities were evaluated in vitro by using Ellman’s method. It was discovered that most of the compounds displayed AChE and/or BuChE inhibitor activity and few compounds were selective against AChE/BuChE. Compound 3c and 3e were the most active compounds in the series against eeAChE and hAChE, respectively. Molecular docking studies and molecular dynamics simulations were also carried out.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2013.06.065