Tehran University of Medical Sciences

Science Communicator Platform

Stay connected! Follow us on X network (Twitter):
Share this content! By
Quinazolinone-Dihydropyrano[3,2-B]Pyran Hybrids As New Α-Glucosidase Inhibitors: Design, Synthesis, Enzymatic Inhibition, Docking Study and Prediction of Pharmacokinetic Publisher Pubmed



Sherafati M1 ; Mirzazadeh R2 ; Barzegari E3 ; Mohammadikhanaposhtani M4 ; Azizian H5 ; Sadegh Asgari M6 ; Hosseini S7 ; Zabihi E4 ; Mojtabavi S8 ; Ali Faramarzi M8 ; Mahdavi M1 ; Larijani B1 ; Rastegar H9 ; Hamedifar H10 Show All Authors
Authors
  1. Sherafati M1
  2. Mirzazadeh R2
  3. Barzegari E3
  4. Mohammadikhanaposhtani M4
  5. Azizian H5
  6. Sadegh Asgari M6
  7. Hosseini S7
  8. Zabihi E4
  9. Mojtabavi S8
  10. Ali Faramarzi M8
  11. Mahdavi M1
  12. Larijani B1
  13. Rastegar H9
  14. Hamedifar H10
  15. Hamed Hajimiri M11

Source: Bioorganic Chemistry Published:2021


Abstract

A series of new quinazolinone-dihydropyrano[3,2-b]pyran derivatives 10A-L were synthesized by simple chemical reactions and were investigated for inhibitory activities against α-glucosidase and α-amylase. New synthesized compounds showed high α-glucosidase inhibition effects in comparison to the standard drug acarbose and were inactive against α-amylase. Among them, the most potent compound was compound 10L (IC50 value = 40.1 ± 0.6 µM) with inhibitory activity around 18.75-fold more than acarboase (IC50 value = 750.0 ± 12.5 µM). This compound was a competitive inhibitor into α-glucosidase. Our obtained experimental results were confirmed by docking studies. Furthermore, the cytotoxicity of the most potent compounds 10L, 10G, and 10N against normal fibroblast cells and in silico druglikeness, ADME, and toxicity prediction of these compounds were also evaluated. © 2021 Elsevier Inc.
Related Docs
View other Related Docs
1. Design and Synthesis of Novel Quinazolinone-1,2,3-Triazole Hybrids As New Anti-Diabetic Agents: In Vitro Α-Glucosidase Inhibition, Kinetic, and Docking Study, Bioorganic Chemistry (2019)
2. Design and Synthesis of Novel Quinazolinone-Pyrazole Derivatives As Potential Α-Glucosidase Inhibitors: Structure-Activity Relationship, Molecular Modeling and Kinetic Study, Bioorganic Chemistry (2021)
3. New Acridine-9-Carboxamide Linked to 1,2,3-Triazole-N-Phenylacetamide Derivatives As Potent Α-Glucosidase Inhibitors: Design, Synthesis, in Vitro, and in Silico Biological Evaluations, Medicinal Chemistry Research (2020)
Experts (# of related papers)
View all Related Experts
Mohammad Ali Faramarzi (18)
Mohammad Mahdavi (18)
Other Related Docs
4. Design, Synthesis and in Vitro Α-Glucosidase Inhibition of Novel Dihydropyrano[3,2-C]Quinoline Derivatives As Potential Anti-Diabetic Agents, Bioorganic Chemistry (2018)
5. Design and Synthesis of New Imidazo[1,2-B]Pyrazole Derivatives, in Vitro Α-Glucosidase Inhibition, Kinetic and Docking Studies, Molecular Diversity (2020)
6. Biscoumarin-1,2,3-Triazole Hybrids As Novel Anti-Diabetic Agents: Design, Synthesis, in Vitro Α-Glucosidase Inhibition, Kinetic, and Docking Studies, Bioorganic Chemistry (2019)
7. 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)
8. 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)
9. 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)
10. Α-Glucosidase and Α-Amylase Inhibition, Molecular Modeling and Pharmacokinetic Studies of New Quinazolinone-1,2,3-Triazole-Acetamide Derivatives, Medicinal Chemistry Research (2021)
11. 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)
12. 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)
13. Design, Synthesis, Biological Evaluation, and Molecular Modeling Studies of Pyrazole-Benzofuran Hybrids As New Α-Glucosidase Inhibitor, Scientific Reports (2021)
14. Novel Coumarin Containing Dithiocarbamate Derivatives As Potent Α-Glucosidase Inhibitors for Management of Type 2 Diabetes, Medicinal Chemistry (2021)
15. Synthesis of the New Tri-Amide Derivatives As Novel Α-Glucosidase Inhibitors by Ugi Four-Component Reaction, Journal of Molecular Structure (2021)
16. Synthesis and Biological Evaluation of New Benzimidazole-1,2,3-Triazole Hybrids As Potential Α-Glucosidase Inhibitors, Bioorganic Chemistry (2020)
17. 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)
18. Design, Synthesis, Characterization, Enzymatic Inhibition Evaluations, and Docking Study of Novel Quinazolinone Derivatives, International Journal of Biological Macromolecules (2021)
19. Design, Synthesis, and Evaluation of Novel Substituted Imidazo[1,2-C]Quinazoline Derivatives As Potential Α-Glucosidase Inhibitors With Bioactivity and Molecular Docking Insights, Scientific Reports (2024)
20. Synthesis, in Vitro Α-Glucosidase Inhibitory Activity and Molecular Dynamics Simulation of Some New Coumarin-Fused 4H-Pyran Derivatives As Potential Anti-Diabetic Agents, Journal of Molecular Structure (2023)