Ugi Adducts: Design and Synthesis of Natural-Based Α-Glucosidase Inhibitors

Ugi Adducts: Design and Synthesis of Natural-Based Α-Glucosidase Inhibitors Publisher

Iraji A^{1, 2} ; Saeedi M^{3, 4} ; Rafieesereshky T⁵ ; Mojtabavi S⁶ ; Faramarzi MA⁶ ; Akbarzadeh T^{4, 5}

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1. Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
2. Central Research Laboratory, Shiraz University of Medical Sciences, Shiraz, Iran
3. Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
4. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran
5. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
6. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, 1417614411, Iran

Source: Letters in Organic Chemistry Published:2022

Abstract

Background: α-Glucosidase inhibitors have been found as the main tool for the treatment of type 2 diabetes. In this respect, the synthesis of a new series of amino-oxoethylcinnamamide derivatives containing α,β-unsaturated carbonyl-based moiety, was developed to be evaluated for their anti-α-glucosidase activity. Methods: The title compounds were synthesized via the Ugi reaction of cinnamic acid, isocyanides, aromatic aldehydes, and amine derivatives at ambient temperature. All newly synthesized derivatives were screened for their in vitro α-glucosidase inhibitory activity. Results: Among synthesized compounds, derivative 5b displayed promising anti-α-glucosidase activity (IC50 = 115.6 µM), approximately 6-fold more potent than the standard drug (acarbose, IC50 = 750.0 μM). Moreover, kinetic characterization of enzyme inhibition was performed to understand the mecha-nism of inhibition. To determine the mode of binding interactions of prepared compounds with the en-zyme, molecular docking studies were also conducted. Conclusion: Ugi products merit to be investigated in anti-diabetic drug discovery developments. This paper is dedicated to our unique teacher of Chemistry and Medicinal Chemistry, Professor Abbas Shafiee (1937-2016). © 2022 Bentham Science Publishers.

Style	Citing Format
MLA	Iraji A, et al.. "Ugi Adducts: Design and Synthesis of Natural-Based Α-Glucosidase Inhibitors." Letters in Organic Chemistry, vol. 19, no. 12, 2022, pp. 1084-1093.
APA	Iraji A, Saeedi M, Rafieesereshky T, Mojtabavi S, Faramarzi MA, Akbarzadeh T (2022). Ugi Adducts: Design and Synthesis of Natural-Based Α-Glucosidase Inhibitors. Letters in Organic Chemistry, 19(12), 1084-1093.
Chicago	Iraji A, Saeedi M, Rafieesereshky T, Mojtabavi S, Faramarzi MA, Akbarzadeh T. "Ugi Adducts: Design and Synthesis of Natural-Based Α-Glucosidase Inhibitors." Letters in Organic Chemistry 19, no. 12 (2022): 1084-1093.
Harvard	Iraji A et al. (2022) 'Ugi Adducts: Design and Synthesis of Natural-Based Α-Glucosidase Inhibitors', Letters in Organic Chemistry, 19(12), pp. 1084-1093.
Vancouver	Iraji A, Saeedi M, Rafieesereshky T, Mojtabavi S, Faramarzi MA, Akbarzadeh T. Ugi Adducts: Design and Synthesis of Natural-Based Α-Glucosidase Inhibitors. Letters in Organic Chemistry. 2022;19(12):1084-1093.
BibTex	@article{ author = {Iraji A and Saeedi M and Rafieesereshky T and Mojtabavi S and Faramarzi MA and Akbarzadeh T}, title = {Ugi Adducts: Design and Synthesis of Natural-Based Α-Glucosidase Inhibitors}, journal = {Letters in Organic Chemistry}, volume = {19}, number = {12}, pages = {1084-1093}, year = {2022} }
RIS	TY - JOUR AU - Iraji A AU - Saeedi M AU - Rafieesereshky T AU - Mojtabavi S AU - Faramarzi MA AU - Akbarzadeh T TI - Ugi Adducts: Design and Synthesis of Natural-Based Α-Glucosidase Inhibitors JO - Letters in Organic Chemistry VL - 19 IS - 12 SP - 1084 EP - 1093 PY - 2022 ER -

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