New 4,5-Diphenylimidazole-Acetamide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Synthesis, in Vitro and in Silico Enzymatic and Toxicity Evaluations

New 4,5-Diphenylimidazole-Acetamide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Synthesis, in Vitro and in Silico Enzymatic and Toxicity Evaluations Publisher

Sepehri N¹ ; Azizian H² ; Ghadimi R³ ; Abedinifar F⁴ ; Mojtabavi S⁵ ; Faramarzi MA⁵ ; Moghadamnia AA⁶ ; Zabihi E⁶ ; Mohebbi G⁷ ; Larijani B⁴ ; Hamedifar H⁸ ; Mohammadikhanaposhtani M⁶ ; Mahdavi M⁴

Show Affiliations

1. Nano Alvand Company, Avicenna Tech Park, Tehran University of Medical Sciences, Tehran, Iran
2. Department of Medicinal Chemistry, School of Pharmacy, Iran University of Medical Sciences, Tehran, Iran
3. Social Determinants of Health Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
4. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
5. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
6. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
7. The Persian Gulf Marine Biotechnology Research Center, The Persian Gulf Biomedical Sciences Research Institute, Bushehr University of Medical Sciences, Bushehr, Iran
8. CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran

Source: Monatshefte fur Chemie Published:2021

Abstract

Herein, a new series of 4,5-diphenylimidazole-acetamide-1,2,3-triazole hybrids as potent α-glucosidase inhibitors was designed and synthesized. All the synthesized compounds exhibited excellent inhibition potencies (IC50 values = 55.6–149.2 μM) against α-glucosidase when compared with the standard inhibitor acarbose (IC50 = 750.0 μM). Among the newly synthesized compounds, 4-methyl, 4-methoxy, and 2,3-dichloro derivatives exhibited the highest anti-α-glucosidase activities and were also non-cytotoxic against human normal dermal fibroblast cells. In silico druglikeness, ADME, and toxicity studies of these compounds were performed and obtained results were compared with acarbose. All the synthesized compounds were also inactive against α-amylase in comparison to acarbose. Kinetic study of the most potent compound, 4-methyl derivative, against α-glucosidase demonstrated that this compound is a competitive inhibitor. Furthermore, in silicoinduced fit docking and molecular dynamic studies were performed to further investigate the interaction, orientation, and conformation of these compounds over the active site of α-glycosidase. Graphic abstract: [Figure not available: see fulltext.] © 2021, Springer-Verlag GmbH Austria, part of Springer Nature.

Style	Citing Format
MLA	Sepehri N, et al.. "New 4,5-Diphenylimidazole-Acetamide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Synthesis, in Vitro and in Silico Enzymatic and Toxicity Evaluations." Monatshefte fur Chemie, vol. 152, no. 6, 2021, pp. 679-693.
APA	Sepehri N, Azizian H, Ghadimi R, Abedinifar F, Mojtabavi S, Faramarzi MA, Moghadamnia AA, Zabihi E, Mohebbi G, Larijani B, Hamedifar H, Mohammadikhanaposhtani M, Mahdavi M (2021). New 4,5-Diphenylimidazole-Acetamide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Synthesis, in Vitro and in Silico Enzymatic and Toxicity Evaluations. Monatshefte fur Chemie, 152(6), 679-693.
Chicago	Sepehri N, Azizian H, Ghadimi R, Abedinifar F, Mojtabavi S, Faramarzi MA, Moghadamnia AA, et al.. "New 4,5-Diphenylimidazole-Acetamide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Synthesis, in Vitro and in Silico Enzymatic and Toxicity Evaluations." Monatshefte fur Chemie 152, no. 6 (2021): 679-693.
Harvard	Sepehri N et al. (2021) 'New 4,5-Diphenylimidazole-Acetamide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Synthesis, in Vitro and in Silico Enzymatic and Toxicity Evaluations', Monatshefte fur Chemie, 152(6), pp. 679-693.
Vancouver	Sepehri N, Azizian H, Ghadimi R, Abedinifar F, Mojtabavi S, Faramarzi MA, et al.. New 4,5-Diphenylimidazole-Acetamide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Synthesis, in Vitro and in Silico Enzymatic and Toxicity Evaluations. Monatshefte fur Chemie. 2021;152(6):679-693.
BibTex	@article{ author = {Sepehri N and Azizian H and Ghadimi R and Abedinifar F and Mojtabavi S and Faramarzi MA and Moghadamnia AA and Zabihi E and Mohebbi G and Larijani B and Hamedifar H and Mohammadikhanaposhtani M and Mahdavi M}, title = {New 4,5-Diphenylimidazole-Acetamide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Synthesis, in Vitro and in Silico Enzymatic and Toxicity Evaluations}, journal = {Monatshefte fur Chemie}, volume = {152}, number = {6}, pages = {679-693}, year = {2021} }
RIS	TY - JOUR AU - Sepehri N AU - Azizian H AU - Ghadimi R AU - Abedinifar F AU - Mojtabavi S AU - Faramarzi MA AU - Moghadamnia AA AU - Zabihi E AU - Mohebbi G AU - Larijani B AU - Hamedifar H AU - Mohammadikhanaposhtani M AU - Mahdavi M TI - New 4,5-Diphenylimidazole-Acetamide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Synthesis, in Vitro and in Silico Enzymatic and Toxicity Evaluations JO - Monatshefte fur Chemie VL - 152 IS - 6 SP - 679 EP - 693 PY - 2021 ER -

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