Synthesis of 4-alkylaminoimidazo[1,2-a]pyridines linked to carbamate moiety as potent α-glucosidase inhibitors
| Autor: | Seyedeh Sara Mirfazli, Mohammad Ali Faramarzi, Mahsa Zardkanlou, Maryam Raeisi-Nafchi, Somayeh Mojtabavi, Tahmineh Akbarzadeh, Sepideh Sobhani, Mina Saeedi |
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| Rok vydání: | 2020 |
| Předmět: |
Carbamate
Stereochemistry medicine.medical_treatment 010402 general chemistry 01 natural sciences Catalysis Inorganic Chemistry Non-competitive inhibition Drug Discovery medicine Moiety Glycoside Hydrolase Inhibitors Physical and Theoretical Chemistry Molecular Biology Acarbose biology 010405 organic chemistry Chemistry Hydrogen bond α glucosidase Organic Chemistry Active site General Medicine Reference drug 0104 chemical sciences biology.protein Information Systems medicine.drug |
| Zdroj: | Molecular Diversity. 25:2399-2409 |
| ISSN: | 1573-501X 1381-1991 |
| Popis: | In this work, various imidazo[1,2-a]pyridines linked to carbamate moiety were designed, synthesized, and evaluated for their α-glucosidase inhibitory activity. Among synthesized compounds, 4-(3-(tert-Butylamino)imidazo[1,2-a]pyridin-2-yl)phenyl p-tolylcarbamate (6d) was the most potent compound (IC50 = 75.6 µM) compared with acarbose as the reference drug (IC50 = 750.0 µM). Kinetic study of compound 6d indicated a competitive inhibition. Also, the molecular docking study suggested desired interactions with the active site residues. In particular, hydrogen bonds and electrostatic interactions constructed by compound 6d afforded well-oriented conformation in the 3A4A active site. |
| Databáze: | OpenAIRE |
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