Design and synthesis of phenoxymethybenzoimidazole incorporating different aryl thiazole-triazole acetamide derivatives as α-glycosidase inhibitors

A novel series of phenoxymethybenzoimidazole derivatives ( 9a-n ) were rationally designed, synthesized, and evaluated for their α-glycosidase inhibitory activity. All tested compounds displayed promising α-glycosidase inhibitory potential with IC 50 values in the range of 6.31 to 49.89 μM compared...

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Published in:Molecular diversity 2022-08, Vol.26 (4), p.1995-2009
Main Authors: Nasli Esfahani, Anita, Iraji, Aida, Alamir, Amir, Moradi, Shahram, Asgari, Mohammad Sadegh, Hosseini, Samanesadat, Mojtabavi, Somayeh, Nasli-Esfahani, Ensieh, Faramarzi, Mohammad Ali, Bandarian, Fatemeh, Larijani, Bagher, Hamedifar, Haleh, Hajimiri, Mir Hamed, Mahdavi, Mohammad
Format: Article
Language:English
Subjects:
Biochemistry
Biomedical and Life Sciences
Biotechnology
Carbohydrates
Design
Diabetes
Endocrinology
Enzyme kinetics
Glucose
Insulin resistance
Life Sciences
Metabolism
Organic Chemistry
Original
Original Article
Pharmaceuticals
Pharmacy
Polymer Sciences
Research centers
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Summary:A novel series of phenoxymethybenzoimidazole derivatives ( 9a-n ) were rationally designed, synthesized, and evaluated for their α-glycosidase inhibitory activity. All tested compounds displayed promising α-glycosidase inhibitory potential with IC 50 values in the range of 6.31 to 49.89 μM compared to standard drug acarbose (IC 50  = 750.0 ± 10.0 μM). Enzyme kinetic studies on 9c , 9g, and 9m as the most potent compounds revealed that these compounds were uncompetitive inhibitors into α-glycosidase. Docking studies confirmed the important role of benzoimidazole and triazole rings of the synthesized compounds to fit properly into the α-glycosidase active site. This study showed that this scaffold can be considered as a highly potent α-glycosidase inhibitor.
ISSN:1381-1991
1573-501X
DOI:10.1007/s11030-021-10310-7