Tehran University of Medical Sciences

Science Communicator Platform

Stay connected! Follow us on X network (Twitter):
Share this content! On (X network) By
Synthesis and Biological Evaluation of New Dihydroindolizino[8,7-B]Indole Derivatives As Novel Α-Glucosidase Inhibitors Publisher



Peytam F1 ; Adib M1 ; Shourgeshty R1 ; Mohammadikhanaposhtani M2 ; Jahani M1 ; Imanparast S3 ; Faramarzi MA3 ; Moghadamnia AA2, 4 ; Larijani B5 ; Mahdavi M5
Authors
Show Affiliations
Authors Affiliations
  1. 1. School of Chemistry, College of Science, University of Tehran, PO Box, 14155-6455, Tehran, Iran
  2. 2. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
  3. 3. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  4. 4. Department of Pharmacology, Faculty of Medical Sciences, Babol University of Medical Sciences, Babol, Iran
  5. 5. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: Journal of Molecular Structure Published:2021


Abstract

Eighteen dihydroindolizino[8,7-b]indole derivatives 4a–r were designed, synthesized and evaluated as new α-glucosidase inhibitors. These derivatives were synthesized by an efficient one-pot two-step reaction under mild condition. All the synthesized compounds were found to be more active than the standard drug acarbose (IC50 = 750.0 ± 1.5 µM) with IC50 values in the range of 107.2 ± 1.0–275.4 ± 1.5 µM. Among the synthesized compounds, diethyl derivative 4o and dimethyl derivative 4 h exhibited the highest anti-α-glucosidase activities (IC50 = 107.2 ± 1.0 and 118.0 ± 0.7 µM, respectively). Kinetic analysis of the compound 4o revealed that this compound is a competitive inhibitor for α-glucosidase with Ki value of 113 µM. Furthermore, the docking study on the compounds 4o and 4 h revealed that these compounds interacted with the important residues in the active site of the homology model of α-glucosidase. © 2020
Related Docs
View other Related Docs
1. New Thiosemicarbazide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, and Biological Evaluation, Journal of Molecular Structure (2019)
2. Synthesis, Molecular Dynamic, and in Silico Study of New Ethyl 4-Arylpyrimido[1,2-B]Indazole-2-Carboxylate: Potential Inhibitors of Α-Glucosidase, Journal of Molecular Structure (2022)
3. Design and Synthesis of 4,5-Diphenyl-Imidazol-1,2,3-Triazole Hybrids As New Anti-Diabetic Agents: In Vitro Α-Glucosidase Inhibition, Kinetic and Docking Studies, Molecular Diversity (2021)
4. 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)
5. 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)
6. Synthesis, Α-Glucosidase Inhibitory Activity and Docking Studies of Novel Ethyl 1,2,3-Triazol-4-Ylmethylthio-5,6-Diphenylpyridazine-4-Carboxylate Derivatives, BMC Chemistry (2023)
7. Design and Synthesis of Novel Quinazolinone-Pyrazole Derivatives As Potential Α-Glucosidase Inhibitors: Structure-Activity Relationship, Molecular Modeling and Kinetic Study, Bioorganic Chemistry (2021)
8. Synthesis and Biological Evaluation of New Benzimidazole-1,2,3-Triazole Hybrids As Potential Α-Glucosidase Inhibitors, Bioorganic Chemistry (2020)
Experts (# of related papers)
View all Related Experts
Mohammad Ali Faramarzi (17)
Mohammad Mahdavi (16)
Other Related Docs
9. Novel Coumarin Containing Dithiocarbamate Derivatives As Potent Α-Glucosidase Inhibitors for Management of Type 2 Diabetes, Medicinal Chemistry (2021)
10. 2,4-Dioxochroman Moiety Linked to 1,2,3-Triazole Derivatives As Novel Α-Glucosidase Inhibitors: Synthesis, in Vitro Biological Evaluation, and Docking Study, Current Organic Chemistry (2020)
11. 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)
12. 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)
13. Synthesis and Biological Evaluation of 12-Aryl-11-Hydroxy-5,6-Dihydropyrrolo[2″,1″:3′,4′]Pyrazino[1′,2′:1,5]Pyrrolo[2,3-D]Pyridazine-8(9H)-One Derivatives As Potential Cytotoxic Agents, ACS Omega (2023)
14. Synthesis, in Vitro Evaluation, and Molecular Docking Studies of Novel Hydrazineylideneindolinone Linked to Phenoxymethyl-1,2,3-Triazole Derivatives As Potential Α-Glucosidase Inhibitors, Bioorganic Chemistry (2021)
15. 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)
16. 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)
17. Synthesis and Biological Evaluation of 2-(2-Methyl-1H-Pyrrol-3-Yl)-2-Oxo-N-(Pyridine-3-Yl) Acetamide Derivatives: In Vitro Α-Glucosidase Inhibition, and Kinetic and Molecular Docking Study, Chemical Papers (2020)
18. 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)
19. Design, Synthesis and Α-Glucosidase Inhibition Study of Novel Pyridazin-Based Derivatives, Medicinal Chemistry Research (2023)
20. 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)
21. Synthesis, In-Vitro Evaluation, Molecular Docking, and Kinetic Studies of Pyridazine-Triazole Hybrid System As Novel Α-Glucosidase Inhibitors, Bioorganic Chemistry (2021)
22. Synthesis of the New Tri-Amide Derivatives As Novel Α-Glucosidase Inhibitors by Ugi Four-Component Reaction, Journal of Molecular Structure (2021)