title: Synthesis, biological activity and molecular modeling studies on 1H-benzimidazole derivatives as acetylcholinesterase inhibitors.
abstract: 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.
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University, 35100 Bornova, Izmir, Turkey.
authors.forename: Ayşe Selcen
authors.initials: AS
authors.lastname: Alpan
authors.forename: Sülünay
authors.initials: S
authors.lastname: Parlar
authors.forename: Luca
authors.initials: L
authors.lastname: Carlino
authors.forename: Ayse Hande
authors.initials: AH
authors.lastname: Tarikogullari
authors.forename: Vildan
authors.initials: V
authors.lastname: Alptüzün
authors.forename: Hasan Semih
authors.initials: HS
authors.lastname: Güneş
mesh_terms: D000110:Acetylcholinesterase / Q000737:chemistry* / Q000378:metabolism; D000818:Animals; D001562:Benzimidazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D001665:Binding Sites; D002091:Butyrylcholinesterase / Q000737:chemistry / Q000378:metabolism; D020134:Catalytic Domain; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D062105:Molecular Docking Simulation; D011485:Protein Binding; D014101:Torpedo / Q000378:metabolism
chemical_list: D001562:Benzimidazoles; D002800:Cholinesterase Inhibitors; C031000:benzimidazole; D000110:Acetylcholinesterase; D002091:Butyrylcholinesterase
keywords: 1H-Benzimidazole; 5,5′-dithiobis(2-nitrobenzoic acid); AChE; AChEI; AD; ATC; Acetylcholinesterase inhibitor; Alzheimer’s disease; Aβ; BuChE; Butyrylcholinesterase inhibitor; CAS; DTNB; Electrophorus electricus AChE; MD; Molecular modeling; PAS; RMSD; Synthesis; TcAChE; Torpedo californica AChE; acetylcholinesterase; acetylcholinesterase inhibitors; acetylthiocholine iodide; butyrylcholinesterase; catalytic active site; eeAChE; hAChE; human AChE; molecular dynamics; peripheral anionic site; root mean square deviation; β-amyloid