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Synthesis, characterization, and molecular docking analysis of novel benzimidazole derivatives as cholinesterase inhibitors.
Bioorg Chem. 2013 Aug; 49:33-9.BC

Abstract

Two series of novel acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors containing benzimidazole core structure were synthesized by a four-step reaction pathway starting from 4-fluoro-3-nitrobenzoic acid as the basic compound. The structure of the novel benzimidazoles was characterized and confirmed by the elemental and mass spectral analyses as well as (1)H NMR spectroscopic data. Of the 34 novel synthesized compounds, three benzimidazoles revealed AChE inhibition with IC50<10 μM. The highest inhibitory activity (IC50=5.12 μM for AChE and IC50=8.63 μM for BChE) corresponds to the compound 5IIc (ethyl 1-(3-(1H-imidazol-1-yl)propyl)-2-(4-nitrophenyl)-1H-benzo[d]imidazole-5-carboxylate). The relationship between lipophilicity and the chemical structures as well as their limited structure-activity relationship was discussed.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Yoon YK
Institute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden, 11800 Penang, Malaysia. kyyeong@gmail.com
Ali MA
No affiliation info available
Wei AC
No affiliation info available
Choon TS
No affiliation info available
Khaw KY
No affiliation info available
Murugaiyah V
No affiliation info available
Osman H
No affiliation info available
Masand VH
No affiliation info available

MeSH

BenzimidazolesCholinesterase InhibitorsCholinesterasesDose-Response Relationship, DrugMolecular Docking SimulationMolecular StructureStructure-Activity Relationship

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23886696

Citation

Yoon, Yeong Keng, et al. "Synthesis, Characterization, and Molecular Docking Analysis of Novel Benzimidazole Derivatives as Cholinesterase Inhibitors." Bioorganic Chemistry, vol. 49, 2013, pp. 33-9.
Yoon YK, Ali MA, Wei AC, et al. Synthesis, characterization, and molecular docking analysis of novel benzimidazole derivatives as cholinesterase inhibitors. Bioorg Chem. 2013;49:33-9.
Yoon, Y. K., Ali, M. A., Wei, A. C., Choon, T. S., Khaw, K. Y., Murugaiyah, V., Osman, H., & Masand, V. H. (2013). Synthesis, characterization, and molecular docking analysis of novel benzimidazole derivatives as cholinesterase inhibitors. Bioorganic Chemistry, 49, 33-9. https://doi.org/10.1016/j.bioorg.2013.06.008
Yoon YK, et al. Synthesis, Characterization, and Molecular Docking Analysis of Novel Benzimidazole Derivatives as Cholinesterase Inhibitors. Bioorg Chem. 2013;49:33-9. PubMed PMID: 23886696.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis, characterization, and molecular docking analysis of novel benzimidazole derivatives as cholinesterase inhibitors. AU - Yoon,Yeong Keng, AU - Ali,Mohamed Ashraf, AU - Wei,Ang Chee, AU - Choon,Tan Soo, AU - Khaw,Kooi-Yeong, AU - Murugaiyah,Vikneswaran, AU - Osman,Hasnah, AU - Masand,Vijay H, Y1 - 2013/07/04/ PY - 2013/02/20/received PY - 2013/05/20/revised PY - 2013/06/17/accepted PY - 2013/7/27/entrez PY - 2013/7/28/pubmed PY - 2016/3/2/medline KW - Acetylcholinesterase KW - Alzheimer’s Disease KW - Benzimidazoles KW - Butyrylcholinesterase KW - ULPRGUULPLUDKL-UHFFFAOYSA-N SP - 33 EP - 9 JF - Bioorganic chemistry JO - Bioorg Chem VL - 49 N2 - Two series of novel acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors containing benzimidazole core structure were synthesized by a four-step reaction pathway starting from 4-fluoro-3-nitrobenzoic acid as the basic compound. The structure of the novel benzimidazoles was characterized and confirmed by the elemental and mass spectral analyses as well as (1)H NMR spectroscopic data. Of the 34 novel synthesized compounds, three benzimidazoles revealed AChE inhibition with IC50<10 μM. The highest inhibitory activity (IC50=5.12 μM for AChE and IC50=8.63 μM for BChE) corresponds to the compound 5IIc (ethyl 1-(3-(1H-imidazol-1-yl)propyl)-2-(4-nitrophenyl)-1H-benzo[d]imidazole-5-carboxylate). The relationship between lipophilicity and the chemical structures as well as their limited structure-activity relationship was discussed. SN - 1090-2120 UR - https://www.unboundmedicine.com/medline/citation/23886696/Synthesis_characterization_and_molecular_docking_analysis_of_novel_benzimidazole_derivatives_as_cholinesterase_inhibitors_ DB - PRIME DP - Unbound Medicine ER -