Tehran University of Medical Sciences

Science Communicator Platform

Stay connected! Follow us on X network (Twitter):
Share this content! By
Synthesis, in Vitro Α-Glucosidase Inhibitory Activities, and Molecular Dynamic Simulations of Novel 4-Hydroxyquinolinone-Hydrazones As Potential Antidiabetic Agents Publisher Pubmed



Shayegan N1 ; Haghipour S1 ; Tanideh N2 ; Moazzam A1 ; Mojtabavi S3 ; Faramarzi MA3 ; Irajie C4 ; Parizad S5 ; Ansari S1 ; Larijani B1 ; Hosseini S1 ; Iraji A2, 6 ; Mahdavi M1
Authors

Source: Scientific Reports Published:2023


Abstract

In the present study, new structural variants of 4-hydroxyquinolinone-hydrazones were designed and synthesized. The structure elucidation of the synthetic derivatives 6a–o was carried out using different spectroscopic techniques including FTIR, 1H-NMR, 13C-NMR, and elemental analysis, and their α-glucosidase inhibitory activity was also determined. The synthetic molecules 6a–o exhibited good α-glucosidase inhibition with IC50 values ranging between 93.5 ± 0.6 to 575.6 ± 0.4 µM as compared to the standard acarbose (IC50 = 752.0 ± 2.0 µM). Structure–activity relationships of this series were established which is mainly based on the position and nature of the substituent on the benzylidene ring. A kinetic study of the active compounds 6l and 6m as the most potent derivatives were also carried out to confirm the mode of inhibition. The binding interactions of the most active compounds within the active site of the enzyme were determined by molecular docking and molecular dynamic simulations. © 2023, The Author(s).
Related Docs
View other Related Docs
1. Synthesis and Structure–Activity Relationship Studies of Benzimidazole-Thioquinoline Derivatives As Α-Glucosidase Inhibitors, Scientific Reports (2023)
2. Synthesis, in Vitro Inhibitor Screening, Structure–Activity Relationship, and Molecular Dynamic Simulation Studies of Novel Thioquinoline Derivatives As Potent Α-Glucosidase Inhibitors, Scientific Reports (2023)
3. Design, Synthesis, and Molecular Docking Studies of Diphenylquinoxaline-6-Carbohydrazide Hybrids As Potent Α-Glucosidase Inhibitors, BMC Chemistry (2022)
Experts (# of related papers)
View all Related Experts
Mohammad Ali Faramarzi (18)
Mohammad Mahdavi (17)
Other Related Docs
4. Synthesis and Bioactivities Evaluation of Quinazolin-4(3H)-One Derivatives As Α-Glucosidase Inhibitors, BMC Chemistry (2022)
5. Design, Synthesis, and in Silico Studies of Quinoline-Based-Benzo[D]Imidazole Bearing Different Acetamide Derivatives As Potent Α-Glucosidase Inhibitors, Scientific Reports (2022)
6. Alpha-Glucosidase Inhibitory and Hypoglycemic Effects of Imidazole-Bearing Thioquinoline Derivatives With Different Substituents: In Silico, in Vitro, and in Vivo Evaluations, Bioorganic Chemistry (2024)
7. Aryl-Quinoline-4-Carbonyl Hydrazone Bearing Different 2-Methoxyphenoxyacetamides As Potent Α-Glucosidase Inhibitors; Molecular Dynamics, Kinetic and Structure–Activity Relationship Studies, Scientific Reports (2024)
8. Design, Synthesis, and in Silico Studies of Benzimidazole Bearing Phenoxyacetamide Derivatives As Α-Glucosidase and Α-Amylase Inhibitors, Journal of Molecular Structure (2022)
9. Evaluation of Novel 2-(Quinoline-2-Ylthio)Acetamide Derivatives Linked to Diphenyl-Imidazole As Α-Glucosidase Inhibitors: Insights From in Silico, in Vitro, and in Vivo Studies on Their Anti-Diabetic Properties, European Journal of Medicinal Chemistry (2024)
10. Design, Synthesis, in Vitro, and in Silico Enzymatic Evaluations of Thieno[2,3-B]Quinoline-Hydrazones As Novel Inhibitors for Α-Glucosidase, Bioorganic Chemistry (2022)
11. Synthesis, in Vitro Potency of Inhibition, Enzyme Kinetics and in Silico Studies of Quinoline-Based Α-Glucosidase Inhibitors, Scientific Reports (2024)
12. Novel N′-Substituted Benzylidene Benzohydrazides Linked to 1,2,3-Triazoles: Potent Α-Glucosidase Inhibitors, Scientific Reports (2023)
13. Design and Synthesis of Novel Quinoline-Piperazines Fused to a Phenylhydrazinecarbothioamide Scaffold As Promising Α-Glucosidase Inhibitors With Anti-Diabetic Potential, Future Medicinal Chemistry (2025)
14. Design and Synthesis of Novel Pyrazole-Phenyl Semicarbazone Derivatives As Potential Α-Glucosidase Inhibitor: Kinetics and Molecular Dynamics Simulation Study, International Journal of Biological Macromolecules (2021)
15. New Solid Phase Methodology for the Synthesis of Biscoumarin Derivatives: Experimental and in Silico Approaches, BMC Chemistry (2022)
16. Imidazo[1,2-C]Quinazolines As a Novel and Potent Scaffold of Α-Glucosidase Inhibitors: Design, Synthesis, Biological Evaluations, and in Silico Studies, Scientific Reports (2023)
17. 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)
18. Pyrano[2,3-B]Chromone Derivatives As Novel Dual Inhibitors of Α-Glucosidase and Α-Amylase: Design, Synthesis, Biological Evaluation, and in Silico Studies, Bioorganic Chemistry (2024)
19. Design, Synthesis, Biological Evaluation, and Molecular Modeling Studies of Pyrazole-Benzofuran Hybrids As New Α-Glucosidase Inhibitor, Scientific Reports (2021)
20. Design, Synthesis, in Vitro Α-Glucosidase Inhibition, Docking, and Molecular Dynamics of New Phthalimide-Benzenesulfonamide Hybrids for Targeting Type 2 Diabetes, Scientific Reports (2022)