Tehran University of Medical Sciences

Science Communicator Platform

Stay connected! Follow us on X network (Twitter):
Share By
Synthesis and Evaluation of 6-Ethoxy-2-Mercaptobenzothiazole Scaffolds As Potential Α-Glucosidase Inhibitors Publisher



Mojibade Balogun M1, 2 ; Shamim S1 ; Mohammed Khan K1, 3 ; Mahdavi M4 ; Salar U5 ; Adebayo Oladosu I2 ; Mohammadikhanaposhtani M6 ; Ali Faramarzi M7 ; Olufunke Moronkola D2 ; Taha M3 ; Rahim F8 ; Perveen S9
Authors

Source: ChemistrySelect Published:2022


Abstract

6-Ethoxy-2-mercapto benzothiazole derivatives 1–26 were synthesized by following two different reaction schemes. Products 1–18 were synthesized by treating 6-ethoxy-2-mercaptobenzothiazole with different phenacyl bromides whereas compounds 19–26 were prepared by the reaction of 6-ethoxy-2-mercaptobenzothiazole with benzyl bromide derivatives under basic conditions. Structural characterization of compounds was performed by mass spectrometric and NMR spectroscopic techniques. Spectroscopic data was well supported to confirm the structures of each analog. All synthetic compounds were subjected to check their potential to inhibit the α-glucosidase enzyme. All scaffolds demonstrated potent inhibitory activity (IC50=60.1±3.6–319.7±7.5 μM) than standard acarbose (IC50=750.0±10.5 μM). Compounds 18 (IC50=60.1±3.6 μM) and 26 (IC50=77.0±4.4 μM) having another electron-rich heterocyclic ring system were identified as the two top-most potent compounds of the series. Kinetic studies ascertained the competitive type inhibition by the most potent analogs. Detailed binding interactions analyses with docking simulations were also carried out which revealed a distinct binding pattern of ligands (synthetic molecules) with the enzyme's active site. © 2022 Wiley-VCH GmbH.
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. Novel N′-Substituted Benzylidene Benzohydrazides Linked to 1,2,3-Triazoles: Potent Α-Glucosidase Inhibitors, Scientific Reports (2023)
3. 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)
Experts (# of related papers)
View all Related Experts
Mohammad Ali Faramarzi (18)
Mohammad Mahdavi (18)
Other Related Docs
4. Benzoylquinazolinone Derivatives As New Potential Antidiabetic Agents: Α-Glucosidase Inhibition, Kinetic, and Docking Studies, Journal of the Chinese Chemical Society (2020)
5. 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)
6. Novel Resorcinol-Based 2-Amino-4H-Chromene-3-Carbonitrile Derivatives As Α-Glucosidase Inhibitors: Synthesis, in Vitro Evaluation, and Molecular Dynamics Simulation Studies, Asian Journal of Organic Chemistry (2025)
7. Rational Design of New Quinoline-Benzimidazole Scaffold Bearing Piperazine Acetamide Derivatives As Antidiabetic Agents, Bioorganic Chemistry (2024)
8. Synthesis of 4-Alkylaminoimidazo[1,2-A]Pyridines Linked to Carbamate Moiety As Potent Α-Glucosidase Inhibitors, Molecular Diversity (2021)
9. Design and Synthesis of Novel 5-Arylisoxazole-1,3,4-Thiadiazole Hybrids As Α-Glucosidase Inhibitors, Letters in Drug Design and Discovery (2021)
10. Synthesis and Biological Evaluation of New Benzimidazole-1,2,3-Triazole Hybrids As Potential Α-Glucosidase Inhibitors, Bioorganic Chemistry (2020)
11. 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)
12. Design of Novel Benzimidazole-Propane Hydrazide Derivatives As Α-Glucosidase and Α-Amylase Inhibitors: In Vitro and in Silico Studies, Medicinal Chemistry Research (2025)
13. A New Route to the Synthesis of 2-Hydrazolyl-4-Thiazolidinone Hybrids, Evaluation of Α-Glucosidase Inhibitory Activity and Molecular Modeling Insights, Heliyon (2024)
14. Design, Synthesis, and in Silico Studies of Benzimidazole Bearing Phenoxyacetamide Derivatives As Α-Glucosidase and Α-Amylase Inhibitors, Journal of Molecular Structure (2022)
15. Design, Synthesis, in Vitro Α-Glucosidase Inhibition, Docking, and Molecular Dynamics of New Phthalimide-Benzenesulfonamide Hybrids for Targeting Type 2 Diabetes, Scientific Reports (2022)
16. Design and Synthesis of Phenoxymethybenzoimidazole Incorporating Different Aryl Thiazole-Triazole Acetamide Derivatives As Α-Glycosidase Inhibitors, Molecular Diversity (2022)
17. Synthesis, in Vitro, and in Silico Evaluation of Indazole Schiff Bases As Potential Α-Glucosidase Inhibitors, Journal of Molecular Structure (2021)
18. Design, Synthesis, and in Silico Studies of Quinoline-Based-Benzo[D]Imidazole Bearing Different Acetamide Derivatives As Potent Α-Glucosidase Inhibitors, Scientific Reports (2022)
19. Design, Synthesis, Biological Evaluation, and Docking Study of New Acridine-9-Carboxamide Linked to 1,2,3-Triazole Derivatives As Antidiabetic Agents Targeting Α-Glucosidase, Journal of Heterocyclic Chemistry (2020)
20. New Benzimidazole–Indole–Amide Derivatives As Potent Α-Glucosidase and Acetylcholinesterase Inhibitors, Archiv der Pharmazie (2025)