A facile approach synthesis of benzoylaryl benzimidazole as potential α-amylase and α-glucosidase inhibitor with antioxidant activity.

Autor: Aroua LM; Department of Chemistry, College of Science, Qassim University, Campus University, King Abdulaziz Road, Al-Malida, 51452-P.O. Box: 6644, Buraydah, Qassim, Saudi Arabia; Laboratory of Organic Structural Chemistry and Macromolecules, Department of Chemistry, Faculty of Sciences of Tunis, Tunis El-Manar University, El Manar I 2092, Tunis, Tunisia; Carthage University, Faculty of Sciences of Bizerte, 7021 Jarzouna, Tunisia. Electronic address: lm.aroua@qu.edu.sa., Almuhaylan HR; Department of Chemistry, College of Science, Qassim University, Campus University, King Abdulaziz Road, Al-Malida, 51452-P.O. Box: 6644, Buraydah, Qassim, Saudi Arabia., Alminderej FM; Department of Chemistry, College of Science, Qassim University, Campus University, King Abdulaziz Road, Al-Malida, 51452-P.O. Box: 6644, Buraydah, Qassim, Saudi Arabia., Messaoudi S; Department of Chemistry, College of Science, Qassim University, Campus University, King Abdulaziz Road, Al-Malida, 51452-P.O. Box: 6644, Buraydah, Qassim, Saudi Arabia; Carthage University, Faculty of Sciences of Bizerte, 7021 Jarzouna, Tunisia., Chigurupati S; Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Qassim University, Buraidah 52571, Saudi Arabia., Al-Mahmoud S; Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Qassim University, Buraidah 52571, Saudi Arabia., Mohammed HA; Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Qassim University, Buraidah 52571, Saudi Arabia; Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt.
Jazyk: angličtina
Zdroj: Bioorganic chemistry [Bioorg Chem] 2021 Sep; Vol. 114, pp. 105073. Date of Electronic Publication: 2021 Jun 12.
DOI: 10.1016/j.bioorg.2021.105073
Abstrakt: Synthetic routes to a series of benzoylarylbenzimidazol 3a-h have been derived from 3,4-diaminobenzophenone and an appropriate arylaldehyde in the presence of ammonium chloride or a mixture of ammonium chloride and sodium metabisulfite as catalyst. The antioxidant activity of targeted compounds 3a-h has been measured by four different methods and the overall antioxidant evaluation of the compounds indicated the significant MCA, FRAP, and (DPPH-SA) of the compounds except for the compound 3h. In vitro antidiabetic assay of α-amylase and α-glucosidase suggest a good to excellent activity for most tested compounds. The target benzimidazole 3f containing hydroxyl motif at para-position of phenyl revealed an important activity inhibitor against α- amylase (IC 50  = 12.09 ± 0.38 µM) and α-glucosidase (IC 50  = 11.02 ± 0.04 µM) comparable to the reference drug acarbose. The results of the anti hyperglycemic activity were supported by means of in silico molecular docking calculations showing strong binding affinity of compounds 3a-h with human pancreatic α-amylase (HPA) and human lysosomal acid-α-glucosidase (HLAG) active sites that confirm a good to excellent activity for most of tested compounds.
(Copyright © 2021 Elsevier Inc. All rights reserved.)
Databáze: MEDLINE
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