Synthesis and Evaluation of 6-Ethoxy-2-Mercaptobenzothiazole Scaffolds As Potential Α-Glucosidase Inhibitors

Synthesis and Evaluation of 6-Ethoxy-2-Mercaptobenzothiazole Scaffolds As Potential Α-Glucosidase Inhibitors Publisher

Mojibade Balogun M^{1, 2} ; Shamim S¹ ; Mohammed Khan K^{1, 3} ; Mahdavi M⁴ ; Salar U⁵ ; Adebayo Oladosu I² ; Mohammadikhanaposhtani M⁶ ; Ali Faramarzi M⁷ ; Olufunke Moronkola D² ; Taha M³ ; Rahim F⁸ ; Perveen S⁹

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1. H. E. J. Research Institute of Chemistry, International Centre for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
2. Department of Chemistry, University of Ibadan, Ibadan, Nigeria
3. Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, P.O. Box 31441, Dammam, Saudi Arabia
4. Endocrinology & Metabolism Research Institute, Tehran University of Medical Sciences, Tehran, Iran
5. Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
6. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
7. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
8. Department of Chemistry, Hazara University, Khyber Pakhtunkhwa, Mansehra, 21300, Pakistan
9. PCSIR Laboratories Complex, Karachi, Shahrah-e-Dr. Salimuzzaman Siddiqui, Karachi, 75280, Pakistan

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.

Style	Citing Format
MLA	Mojibade Balogun M, et al.. "Synthesis and Evaluation of 6-Ethoxy-2-Mercaptobenzothiazole Scaffolds As Potential Α-Glucosidase Inhibitors." ChemistrySelect, vol. 7, no. 26, 2022, pp. -.
APA	Mojibade Balogun M, Shamim S, Mohammed Khan K, Mahdavi M, Salar U, Adebayo Oladosu I, Mohammadikhanaposhtani M, Ali Faramarzi M, Olufunke Moronkola D, Taha M, Rahim F, Perveen S (2022). Synthesis and Evaluation of 6-Ethoxy-2-Mercaptobenzothiazole Scaffolds As Potential Α-Glucosidase Inhibitors. ChemistrySelect, 7(26), -.
Chicago	Mojibade Balogun M, Shamim S, Mohammed Khan K, Mahdavi M, Salar U, Adebayo Oladosu I, Mohammadikhanaposhtani M, et al.. "Synthesis and Evaluation of 6-Ethoxy-2-Mercaptobenzothiazole Scaffolds As Potential Α-Glucosidase Inhibitors." ChemistrySelect 7, no. 26 (2022): -.
Harvard	Mojibade Balogun M et al. (2022) 'Synthesis and Evaluation of 6-Ethoxy-2-Mercaptobenzothiazole Scaffolds As Potential Α-Glucosidase Inhibitors', ChemistrySelect, 7(26), pp. -.
Vancouver	Mojibade Balogun M, Shamim S, Mohammed Khan K, Mahdavi M, Salar U, Adebayo Oladosu I, et al.. Synthesis and Evaluation of 6-Ethoxy-2-Mercaptobenzothiazole Scaffolds As Potential Α-Glucosidase Inhibitors. ChemistrySelect. 2022;7(26):-.
BibTex	@article{ author = {Mojibade Balogun M and Shamim S and Mohammed Khan K and Mahdavi M and Salar U and Adebayo Oladosu I and Mohammadikhanaposhtani M and Ali Faramarzi M and Olufunke Moronkola D and Taha M and Rahim F and Perveen S}, title = {Synthesis and Evaluation of 6-Ethoxy-2-Mercaptobenzothiazole Scaffolds As Potential Α-Glucosidase Inhibitors}, journal = {ChemistrySelect}, volume = {7}, number = {26}, pages = {-}, year = {2022} }
RIS	TY - JOUR AU - Mojibade Balogun M AU - Shamim S AU - Mohammed Khan K AU - Mahdavi M AU - Salar U AU - Adebayo Oladosu I AU - Mohammadikhanaposhtani M AU - Ali Faramarzi M AU - Olufunke Moronkola D AU - Taha M AU - Rahim F AU - Perveen S TI - Synthesis and Evaluation of 6-Ethoxy-2-Mercaptobenzothiazole Scaffolds As Potential Α-Glucosidase Inhibitors JO - ChemistrySelect VL - 7 IS - 26 SP - EP - PY - 2022 ER -

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