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2-Aryl benzimidazoles: Synthesis, In vitro α-amylase inhibitory activity, and molecular docking study.
Eur J Med Chem. 2018 Apr 25; 150:248-260.EJ

Abstract

Despite of many diverse biological activities exhibited by benzimidazole scaffold, it is rarely explored for the α-amylase inhibitory activity. For that purpose, 2-aryl benzimidazole derivatives 1-45 were synthesized and screened for in vitro α-amylase inhibitory activity. Structures of all synthetic compounds were deduced by various spectroscopic techniques. All compounds revealed inhibition potential with IC50 values of 1.48 ± 0.38-2.99 ± 0.14 μM, when compared to the standard acarbose (IC50 = 1.46 ± 0.26 μM). Limited SAR suggested that the variation in the inhibitory activities of the compounds are the result of different substitutions on aryl ring. In order to rationalize the binding interactions of most active compounds with the active site of α-amylase enzyme, in silico study was conducted.

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Authors+Show Affiliations

Adegboye AA
Department of Chemistry, University of Ibadan, Ibadan, Nigeria.
Khan KM
H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan; Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, P.O. Box 1982, Dammam 31441, Saudi Arabia. Electronic address: khalid.khan@iccs.edu.
Salar U
H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan.
Aboaba SA
Department of Chemistry, University of Ibadan, Ibadan, Nigeria.
Kanwal
H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan.
Chigurupati S
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, AIMST University, Semeling, 08100 Bedong, Kedah, Malaysia.
Fatima I
H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan.
Taha M
Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, P.O. Box 1982, Dammam 31441, Saudi Arabia.
Wadood A
Department of Biochemistry, Computational Medicinal Chemistry Laboratory, UCSS, Abdul Wali Khan University, Mardan, Pakistan.
Mohammad JI
Department of Pharmacology, Faculty of Medicine, Cyberjaya University College of Medical Sciences, CUCMS, Cyberjaya, 63000, Malaysia.
Khan H
Department of Biochemistry, Computational Medicinal Chemistry Laboratory, UCSS, Abdul Wali Khan University, Mardan, Pakistan.
Perveen S
PCSIR Laboratories Complex, Karachi, Shahrah-e-Dr. SalimuzzamanSiddiqui, Karachi, 75280, Pakistan.

MeSH

BenzimidazolesDose-Response Relationship, DrugGlycoside Hydrolase InhibitorsMolecular Docking SimulationMolecular StructureStructure-Activity Relationshipalpha-Amylases

Pub Type(s)

Journal Article

Language

eng

PubMed ID

29533872

Citation

Adegboye, Akande Akinsola, et al. "2-Aryl Benzimidazoles: Synthesis, in Vitro Α-amylase Inhibitory Activity, and Molecular Docking Study." European Journal of Medicinal Chemistry, vol. 150, 2018, pp. 248-260.
Adegboye AA, Khan KM, Salar U, et al. 2-Aryl benzimidazoles: Synthesis, In vitro α-amylase inhibitory activity, and molecular docking study. Eur J Med Chem. 2018;150:248-260.
Adegboye, A. A., Khan, K. M., Salar, U., Aboaba, S. A., Kanwal, ., Chigurupati, S., Fatima, I., Taha, M., Wadood, A., Mohammad, J. I., Khan, H., & Perveen, S. (2018). 2-Aryl benzimidazoles: Synthesis, In vitro α-amylase inhibitory activity, and molecular docking study. European Journal of Medicinal Chemistry, 150, 248-260. https://doi.org/10.1016/j.ejmech.2018.03.011
Adegboye AA, et al. 2-Aryl Benzimidazoles: Synthesis, in Vitro Α-amylase Inhibitory Activity, and Molecular Docking Study. Eur J Med Chem. 2018 Apr 25;150:248-260. PubMed PMID: 29533872.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 2-Aryl benzimidazoles: Synthesis, In vitro α-amylase inhibitory activity, and molecular docking study. AU - Adegboye,Akande Akinsola, AU - Khan,Khalid Mohammed, AU - Salar,Uzma, AU - Aboaba,Sherifat Adeyinka, AU - Kanwal,, AU - Chigurupati,Sridevi, AU - Fatima,Itrat, AU - Taha,Mohammad, AU - Wadood,Abdul, AU - Mohammad,Jahidul Isalm, AU - Khan,Huma, AU - Perveen,Shahnaz, Y1 - 2018/03/06/ PY - 2017/12/20/received PY - 2018/02/18/revised PY - 2018/03/02/accepted PY - 2018/3/14/pubmed PY - 2018/4/27/medline PY - 2018/3/14/entrez KW - Benzimidazole KW - In silico KW - In vitro KW - Structure-activity relationship (SAR) KW - α-Amylase SP - 248 EP - 260 JF - European journal of medicinal chemistry JO - Eur J Med Chem VL - 150 N2 - Despite of many diverse biological activities exhibited by benzimidazole scaffold, it is rarely explored for the α-amylase inhibitory activity. For that purpose, 2-aryl benzimidazole derivatives 1-45 were synthesized and screened for in vitro α-amylase inhibitory activity. Structures of all synthetic compounds were deduced by various spectroscopic techniques. All compounds revealed inhibition potential with IC50 values of 1.48 ± 0.38-2.99 ± 0.14 μM, when compared to the standard acarbose (IC50 = 1.46 ± 0.26 μM). Limited SAR suggested that the variation in the inhibitory activities of the compounds are the result of different substitutions on aryl ring. In order to rationalize the binding interactions of most active compounds with the active site of α-amylase enzyme, in silico study was conducted. SN - 1768-3254 UR - https://www.unboundmedicine.com/medline/citation/29533872/2_Aryl_benzimidazoles:_Synthesis_In_vitro_α_amylase_inhibitory_activity_and_molecular_docking_study_ DB - PRIME DP - Unbound Medicine ER -