Design and synthesis of phenoxymethybenzoimidazole incorporating different aryl thiazole-triazole acetamide derivatives as α-glycosidase inhibitors
| Autor: | Somayeh Mojtabavi, Fatemeh Bandarian, Amir Alamir, Aida Iraji, Mohammad Ali Faramarzi, Mir Hamed Hajimiri, Mohammad Sadegh Asgari, Haleh Hamedifar, Mohammad Mahdavi, Ensieh Nasli-Esfahani, Anita Nasli Esfahani, Samanesadat Hosseini, Bagher Larijani, Shahram Moradi |
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| Rok vydání: | 2021 |
| Předmět: |
Benzimidazole
Triazole Triazole-acetamide Catalysis Inorganic Chemistry Synthesis Structure-Activity Relationship chemistry.chemical_compound Acetamides Drug Discovery medicine Glycoside Hydrolase Inhibitors Physical and Theoretical Chemistry Thiazole Molecular Biology Acarbose α-Glycosidase Molecular Structure biology Aryl Organic Chemistry Active site alpha-Glucosidases General Medicine Triazoles Combinatorial chemistry Molecular Docking Simulation Enzyme inhibition Kinetics Thiazoles chemistry Docking (molecular) biology.protein Original Article Acetamide Information Systems medicine.drug |
| Zdroj: | Molecular Diversity |
| ISSN: | 1573-501X 1381-1991 |
| DOI: | 10.1007/s11030-021-10310-7 |
| Popis: | 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 IC50 values in the range of 6.31 to 49.89 μM compared to standard drug acarbose (IC50 = 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. Supplementary Information The online version contains supplementary material available at 10.1007/s11030-021-10310-7. |
| Databáze: | OpenAIRE |
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