Quinazolinone-Dihydropyrano[3,2-B]Pyran Hybrids As New Α-Glucosidase Inhibitors: Design, Synthesis, Enzymatic Inhibition, Docking Study and Prediction of Pharmacokinetic

Science Communicator Platform

Stay connected! Follow us on X network (Twitter):

Share this content! On (X network) 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

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
Hamed Hajimiri M¹¹

Show Affiliations

1. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
2. Department of Biochemistry, Pasteur Institute of Iran, Tehran, Iran
3. Medical Biology Research Center, Health Technology Institute, Kermanshah University of Medical Sciences, Kermanshah, Iran
4. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
5. Department of Medicinal Chemistry, School of Pharmacy, Iran University of Medical Sciences, Tehran, Iran
6. Department of Chemistry, Iran University of Science and Technology, Tehran, Iran
7. Department of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran
8. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
9. Cosmetic Products Research Center, Iranian Food and Drug Administration, MOHE, Tehran, Iran
10. CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran
11. Nano Alvand Company, Avicenna Tech Park, Tehran University of Medical Sciences, Tehran, Iran

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)

4. 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)

5. Α-Glucosidase and Α-Amylase Inhibition, Molecular Modeling and Pharmacokinetic Studies of New Quinazolinone-1,2,3-Triazole-Acetamide Derivatives, Medicinal Chemistry Research (2021)

6. 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)

7. Novel Coumarin Containing Dithiocarbamate Derivatives As Potent Α-Glucosidase Inhibitors for Management of Type 2 Diabetes, Medicinal Chemistry (2021)

8. 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)

Experts (# of related papers)

View all Related Experts

Mohammad Mahdavi (25)

Mohammad Ali Faramarzi (24)

Other Related Docs

9. Design and Synthesis of New Imidazo[1,2-B]Pyrazole Derivatives, in Vitro Α-Glucosidase Inhibition, Kinetic and Docking Studies, Molecular Diversity (2020)

10. In Silico and in Vitro Studies of Thiosemicarbazone-Indole Hybrid Compounds As Potent Α-Glycosidase Inhibitors, Computational Biology and Chemistry (2022)

11. 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)

12. New Phthalimide-Benzamide-1,2,3-Triazole Hybrids; Design, Synthesis, Α-Glucosidase Inhibition Assay, and Docking Study, Medicinal Chemistry Research (2020)

13. 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)

14. Design, Synthesis and in Vitro Α-Glucosidase Inhibition of Novel Dihydropyrano[3,2-C]Quinoline Derivatives As Potential Anti-Diabetic Agents, Bioorganic Chemistry (2018)

15. Synthesis, Molecular Docking and Α-Glucosidase Inhibitory Activity Study of 2,4,6-Triaryl Pyrimidine Derivatives, Letters in Drug Design and Discovery (2020)

16. Synthesis and Biological Evaluation of New Benzimidazole-1,2,3-Triazole Hybrids As Potential Α-Glucosidase Inhibitors, Bioorganic Chemistry (2020)

17. In Vivo and in Silico Evaluations of a Synthetic Pyrano[3,2-C]Quinoline Derivative As a Potent Anti-Diabetic Agent, Journal of Diabetes and Metabolic Disorders (2023)

18. 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)

19. Design, Synthesis, Biological Evaluation, and Molecular Modeling Studies of Pyrazole-Benzofuran Hybrids As New Α-Glucosidase Inhibitor, Scientific Reports (2021)

20. Synthesis of the New Tri-Amide Derivatives As Novel Α-Glucosidase Inhibitors by Ugi Four-Component Reaction, Journal of Molecular Structure (2021)

21. Design, Synthesis, Characterization, Enzymatic Inhibition Evaluations, and Docking Study of Novel Quinazolinone Derivatives, International Journal of Biological Macromolecules (2021)

22. Novel Aryl(4-Phenylpiperazin-1-Yl)Methanethione Derivatives As New Anti-Alzheimer Agents: Design, Synthesis, in Vitro and in Silico Assays, Journal of Molecular Structure (2022)

23. An Efficient and Targeted Synthetic Approach Towards New Highly Substituted 6-Amino-Pyrazolo[1,5-A]Pyrimidines With Α-Glucosidase Inhibitory Activity, Scientific Reports (2020)

24. 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)

25. A Review on Synthesis, Mechanism of Action, and Structure-Activity Relationships of 1,2,3-Triazole-Based Α-Glucosidase Inhibitors As Promising Anti-Diabetic Agents, Journal of Molecular Structure (2022)

26. 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)

27. Synthesis and Anticancer Activity of N -Substituted 2-Arylquinazolinones Bearing Trans -Stilbene Scaffold, European Journal of Medicinal Chemistry (2015)

28. 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)

29. 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)

Style	Citing Format
MLA	Sherafati M, et al.. "Quinazolinone-Dihydropyrano[3,2-B]Pyran Hybrids As New Α-Glucosidase Inhibitors: Design, Synthesis, Enzymatic Inhibition, Docking Study and Prediction of Pharmacokinetic." Bioorganic Chemistry, vol. 109, no. , 2021, pp. -.
APA	Sherafati M, Mirzazadeh R, Barzegari E, Mohammadikhanaposhtani M, Azizian H, Sadegh Asgari M, Hosseini S, Zabihi E, Mojtabavi S, Ali Faramarzi M, Mahdavi M, Larijani B, Rastegar H, Hamedifar H, Hamed Hajimiri M (2021). Quinazolinone-Dihydropyrano[3,2-B]Pyran Hybrids As New Α-Glucosidase Inhibitors: Design, Synthesis, Enzymatic Inhibition, Docking Study and Prediction of Pharmacokinetic. Bioorganic Chemistry, 109(), -.
Chicago	Sherafati M, Mirzazadeh R, Barzegari E, Mohammadikhanaposhtani M, Azizian H, Sadegh Asgari M, Hosseini S, et al.. "Quinazolinone-Dihydropyrano[3,2-B]Pyran Hybrids As New Α-Glucosidase Inhibitors: Design, Synthesis, Enzymatic Inhibition, Docking Study and Prediction of Pharmacokinetic." Bioorganic Chemistry 109, no. (2021): -.
Harvard	Sherafati M et al. (2021) 'Quinazolinone-Dihydropyrano[3,2-B]Pyran Hybrids As New Α-Glucosidase Inhibitors: Design, Synthesis, Enzymatic Inhibition, Docking Study and Prediction of Pharmacokinetic', Bioorganic Chemistry, 109(), pp. -.
Vancouver	Sherafati M, Mirzazadeh R, Barzegari E, Mohammadikhanaposhtani M, Azizian H, Sadegh Asgari M, et al.. Quinazolinone-Dihydropyrano[3,2-B]Pyran Hybrids As New Α-Glucosidase Inhibitors: Design, Synthesis, Enzymatic Inhibition, Docking Study and Prediction of Pharmacokinetic. Bioorganic Chemistry. 2021;109():-.
BibTex	@article{ author = {Sherafati M and Mirzazadeh R and Barzegari E and Mohammadikhanaposhtani M and Azizian H and Sadegh Asgari M and Hosseini S and Zabihi E and Mojtabavi S and Ali Faramarzi M and Mahdavi M and Larijani B and Rastegar H and Hamedifar H and Hamed Hajimiri M}, title = {Quinazolinone-Dihydropyrano[3,2-B]Pyran Hybrids As New Α-Glucosidase Inhibitors: Design, Synthesis, Enzymatic Inhibition, Docking Study and Prediction of Pharmacokinetic}, journal = {Bioorganic Chemistry}, volume = {109}, number = {}, pages = {-}, year = {2021} }
RIS	TY - JOUR AU - Sherafati M AU - Mirzazadeh R AU - Barzegari E AU - Mohammadikhanaposhtani M AU - Azizian H AU - Sadegh Asgari M AU - Hosseini S AU - Zabihi E AU - Mojtabavi S AU - Ali Faramarzi M AU - Mahdavi M AU - Larijani B AU - Rastegar H AU - Hamedifar H AU - Hamed Hajimiri M TI - Quinazolinone-Dihydropyrano[3,2-B]Pyran Hybrids As New Α-Glucosidase Inhibitors: Design, Synthesis, Enzymatic Inhibition, Docking Study and Prediction of Pharmacokinetic JO - Bioorganic Chemistry VL - 109 IS - SP - EP - PY - 2021 ER -

Science Communicator Platform

Authors

Authors Affiliations

Abstract