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Synthesis, biological activity and molecular modeling studies on 1H-benzimidazole derivatives as acetylcholinesterase inhibitors.
Bioorg Med Chem. 2013 Sep 01; 21(17):4928-37.BM

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+Show Affiliations

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University, 35100 Bornova, Izmir, Turkey.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

23891231

Citation

Alpan, Ayşe Selcen, et al. "Synthesis, Biological Activity and Molecular Modeling Studies On 1H-benzimidazole Derivatives as Acetylcholinesterase Inhibitors." Bioorganic & Medicinal Chemistry, vol. 21, no. 17, 2013, pp. 4928-37.
Alpan AS, Parlar S, Carlino L, et al. Synthesis, biological activity and molecular modeling studies on 1H-benzimidazole derivatives as acetylcholinesterase inhibitors. Bioorg Med Chem. 2013;21(17):4928-37.
Alpan, A. S., Parlar, S., Carlino, L., Tarikogullari, A. H., Alptüzün, V., & Güneş, H. S. (2013). Synthesis, biological activity and molecular modeling studies on 1H-benzimidazole derivatives as acetylcholinesterase inhibitors. Bioorganic & Medicinal Chemistry, 21(17), 4928-37. https://doi.org/10.1016/j.bmc.2013.06.065
Alpan AS, et al. Synthesis, Biological Activity and Molecular Modeling Studies On 1H-benzimidazole Derivatives as Acetylcholinesterase Inhibitors. Bioorg Med Chem. 2013 Sep 1;21(17):4928-37. PubMed PMID: 23891231.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis, biological activity and molecular modeling studies on 1H-benzimidazole derivatives as acetylcholinesterase inhibitors. AU - Alpan,Ayşe Selcen, AU - Parlar,Sülünay, AU - Carlino,Luca, AU - Tarikogullari,Ayse Hande, AU - Alptüzün,Vildan, AU - Güneş,Hasan Semih, Y1 - 2013/07/10/ PY - 2013/05/09/received PY - 2013/06/26/revised PY - 2013/06/27/accepted PY - 2013/7/30/entrez PY - 2013/7/31/pubmed PY - 2014/3/19/medline KW - 1H-Benzimidazole KW - 5,5′-dithiobis(2-nitrobenzoic acid) KW - AChE KW - AChEI KW - AD KW - ATC KW - Acetylcholinesterase inhibitor KW - Alzheimer’s disease KW - Aβ KW - BuChE KW - Butyrylcholinesterase inhibitor KW - CAS KW - DTNB KW - Electrophorus electricus AChE KW - MD KW - Molecular modeling KW - PAS KW - RMSD KW - Synthesis KW - TcAChE KW - Torpedo californica AChE KW - acetylcholinesterase KW - acetylcholinesterase inhibitors KW - acetylthiocholine iodide KW - butyrylcholinesterase KW - catalytic active site KW - eeAChE KW - hAChE KW - human AChE KW - molecular dynamics KW - peripheral anionic site KW - root mean square deviation KW - β-amyloid SP - 4928 EP - 37 JF - Bioorganic & medicinal chemistry JO - Bioorg Med Chem VL - 21 IS - 17 N2 - 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. SN - 1464-3391 UR - https://www.unboundmedicine.com/medline/citation/23891231/Synthesis_biological_activity_and_molecular_modeling_studies_on_1H_benzimidazole_derivatives_as_acetylcholinesterase_inhibitors_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0968-0896(13)00605-6 DB - PRIME DP - Unbound Medicine ER -