Tehran University of Medical Sciences

Science Communicator Platform

Stay connected! Follow us on X network (Twitter):
Share this content! By
Design, Synthesis, and Α-Glucosidase-Inhibitory Activity of Phenoxy-Biscoumarin–N-Phenylacetamide Hybrids Publisher Pubmed



Ansari S1 ; Azizian H2 ; Pedrood K3 ; Yavari A3 ; Mojtabavi S4 ; Faramarzi MA4 ; Golshani S4 ; Hosseini S5 ; Biglar M3 ; Larijani B3 ; Rastegar H6 ; Hamedifar H1 ; Mohammadikhanaposhtani M7 ; Mahdavi M3
Authors

Source: Archiv der Pharmazie Published:2021


Abstract

Thirteen new phenoxy-biscoumarin–N-phenylacetamide derivatives (7a–m) were designed based on a molecular hybridization approach as new α-glucosidase inhibitors. These compounds were synthesized with high yields and evaluated in vitro for their inhibitory activity against yeast α-glucosidase. The obtained results revealed that a significant proportion of the synthesized compounds showed considerable α-glucosidase-inhibitory activity in comparison to acarbose as a positive control. Representatively, 2-(4-(bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)phenoxy)-N-(4-bromophenyl)acetamide (7f), with IC50 = 41.73 ± 0.38 µM against α-glucosidase, was around 18 times more potent than acarbose (IC50 = 750.0 ± 10.0 µM). This compound was a competitive α-glucosidase inhibitor. Molecular modeling and dynamic simulation of these compounds confirmed the obtained results through in vitro experiments. Prediction of the druglikeness/ADME/toxicity of the compound 7f and comparison with the standard drug acarbose showed that the new compound 7f was probably better than the standard drug in terms of toxicity. © 2021 Deutsche Pharmazeutische Gesellschaft
Related Docs
View other Related Docs
1. Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations, ChemistrySelect (2023)
2. Design of New Α-Glucosidase Inhibitors Based on the Bis-4-Hydroxycoumarin Skeleton: Synthesis, Evaluation, and in Silico Studies, Scientific Reports (2024)
3. Design, Synthesis, in Vitro, and in Silico Biological Evaluations of Coumarin-Indole Hybrids As New Anti-Α-Glucosidase Agents, BMC Chemistry (2022)
Experts (# of related papers)
View all Related Experts
Mohammad Ali Faramarzi (19)
Mohammad Mahdavi (18)
Other Related Docs
4. Design, Synthesis and Biological Evaluation of Novel Phthalimide-Schiff Base-Coumarin Hybrids As Potent Α-Glucosidase Inhibitors, Chemical Papers (2020)
5. Indole-Carbohydrazide Linked Phenoxy-1,2,3-Triazole-N-Phenylacetamide Derivatives As Potent Α-Glucosidase Inhibitors: Design, Synthesis, in Vitro Α-Glucosidase Inhibition, and Computational Studies, BMC Chemistry (2023)
6. New 4,5-Diphenylimidazole-Acetamide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Synthesis, in Vitro and in Silico Enzymatic and Toxicity Evaluations, Monatshefte fur Chemie (2021)
7. Synthesis and Structure–Activity Relationship Studies of Benzimidazole-Thioquinoline Derivatives As Α-Glucosidase Inhibitors, Scientific Reports (2023)
8. Pyrano[3,2-C]Quinoline Derivatives As New Class of Α-Glucosidase Inhibitors to Treat Type 2 Diabetes: Synthesis, in Vitro Biological Evaluation and Kinetic Study, Medicinal Chemistry (2019)
9. Novel N′-Substituted Benzylidene Benzohydrazides Linked to 1,2,3-Triazoles: Potent Α-Glucosidase Inhibitors, Scientific Reports (2023)
10. New Phenylthiosemicarbazide-Phenoxy-1,2,3-Triazole-N-Phenylacetamides As Dual Inhibitors Against Α-Glucosidase and Ptp-1B for the Treatment of Type 2 Diabetes, Archiv der Pharmazie (2024)
11. Design, Synthesis, Molecular Docking, and in Vitro Α-Glucosidase Inhibitory Activities of Novel 3-Amino-2,4-Diarylbenzo[4,5]Imidazo[1,2-A]Pyrimidines Against Yeast and Rat Α-Glucosidase, Scientific Reports (2021)
12. Design, Synthesis, in Vitro, and in Silico Studies of Novel Diarylimidazole-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors, Bioorganic and Medicinal Chemistry (2019)
13. New 4-Phenylpiperazine-Carbodithioate-N-Phenylacetamide Hybrids: Synthesis, in Vitro and in Silico Evaluations Against Cholinesterase and Α-Glucosidase Enzymes, Archiv der Pharmazie (2022)
14. Benzoylquinazolinone Derivatives As New Potential Antidiabetic Agents: Α-Glucosidase Inhibition, Kinetic, and Docking Studies, Journal of the Chinese Chemical Society (2020)
15. 1-Phenyl-Β-Carboline-3-Carboxamide-1,2,3-Triazole-N-Phenylacetamide Hybrids As New Α-Glucosidase Inhibitors, Scientific Reports (2025)
16. Novel Pyrano[3,2-C]Quinoline-1,2,3-Triazole Hybrids As Potential Anti-Diabetic Agents: In Vitro Α-Glucosidase Inhibition, Kinetic, and Molecular Dynamics Simulation, ACS Omega (2023)
17. Design, Synthesis and in Vitro Α-Glucosidase Inhibition of Novel Coumarin-Pyridines As Potent Antidiabetic Agents, New Journal of Chemistry (2018)
18. Synthesis, in Vitro and in Silico Enzymatic Inhibition Assays, and Toxicity Evaluations of New 4,5-Diphenylimidazole-N-Phenylacetamide Derivatives As Potent Α-Glucosidase Inhibitors, Medicinal Chemistry Research (2021)
19. Design and Synthesis of New Fused Carbazole-Imidazole Derivatives As Anti-Diabetic Agents: In Vitro Α-Glucosidase Inhibition, Kinetic, and in Silico Studies, Bioorganic and Medicinal Chemistry Letters (2019)
20. Design, Synthesis, Docking Study, Α-Glucosidase Inhibition, and Cytotoxic Activities of Acridine Linked to Thioacetamides As Novel Agents in Treatment of Type 2 Diabetes, Bioorganic Chemistry (2018)