Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations

Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations Publisher

Gavanrudi MR¹ ; Halimi M² ; Najafzadehvarzi H³ ; Alikhani M⁴ ; Moazzam A⁵ ; Farzipour S⁶ ; Hosseini S⁷ ; Mojtabavi S⁸ ; Faramarzi MA⁸ ; Nasliesfahani E⁹ ; Mohammadikhanaposhtani M³ ; Mahdavi M⁵

Show Affiliations

1. Department of Medicinal Chemistry, Faculty of Pharmacy, Islamic Azad University, Ayatollah Amoli Branch, Amol, Iran
2. Department of Biology, Babol Branch, Islamic Azad University, Babol, Iran
3. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
4. Department of Internal Medicine, School of Medicine, Rheumatology Research Center Shariati Hospital, Tehran University of Medical Sciences, Iran
5. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
6. Cardiovascular Diseases Research Center, Department of Cardiology, Heshmat Hospital, School of Medicine, Guilan University of Medical Sciences, Rasht, Iran
7. Shahid Beheshti University of Medical Sciences, Tehran, Iran
8. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
9. Diabetes Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: ChemistrySelect Published:2023

Abstract

Thirteen new derivatives of the phthalimide-1,2,3-triazole-N-phenylacetamide hybrids were synthesized via simple chemical reactions. These hybrids were evaluated for their inhibitory potential against α-glucosidase in vitro and in silico. Among these thirteen derivatives, seven compounds showed excellent inhibition against studied enzyme (IC50 values=1.30−31.7 μM) as compared to positive control acarbose (IC50 value=750.1 μM) and among them, compound with 2,4-dichloro substituent on the phenyl ring of N-phenylacetamide moiety was identified as the most potent inhibitor against α-glucosidase. This compound was almost 577-fold more active than acarbose. Kinetic study on the most potent compound demonstrated that this compound is a competitive α-glucosidase inhibitor. To understand the interaction mode, stability, and flexibility of the most potent compounds, molecular docking and molecular dynamics studies were conducted. Furthermore, the drug-likeness, pharmacokinetic, and toxicity properties of the title compounds were predicted by in silico studies. © 2023 Wiley-VCH GmbH.

Style	Citing Format
MLA	Gavanrudi MR, et al.. "Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations." ChemistrySelect, vol. 8, no. 26, 2023, pp. -.
APA	Gavanrudi MR, Halimi M, Najafzadehvarzi H, Alikhani M, Moazzam A, Farzipour S, Hosseini S, Mojtabavi S, Faramarzi MA, Nasliesfahani E, Mohammadikhanaposhtani M, Mahdavi M (2023). Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations. ChemistrySelect, 8(26), -.
Chicago	Gavanrudi MR, Halimi M, Najafzadehvarzi H, Alikhani M, Moazzam A, Farzipour S, Hosseini S, et al.. "Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations." ChemistrySelect 8, no. 26 (2023): -.
Harvard	Gavanrudi MR et al. (2023) 'Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations', ChemistrySelect, 8(26), pp. -.
Vancouver	Gavanrudi MR, Halimi M, Najafzadehvarzi H, Alikhani M, Moazzam A, Farzipour S, et al.. Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations. ChemistrySelect. 2023;8(26):-.
BibTex	@article{ author = {Gavanrudi MR and Halimi M and Najafzadehvarzi H and Alikhani M and Moazzam A and Farzipour S and Hosseini S and Mojtabavi S and Faramarzi MA and Nasliesfahani E and Mohammadikhanaposhtani M and Mahdavi M}, title = {Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations}, journal = {ChemistrySelect}, volume = {8}, number = {26}, pages = {-}, year = {2023} }
RIS	TY - JOUR AU - Gavanrudi MR AU - Halimi M AU - Najafzadehvarzi H AU - Alikhani M AU - Moazzam A AU - Farzipour S AU - Hosseini S AU - Mojtabavi S AU - Faramarzi MA AU - Nasliesfahani E AU - Mohammadikhanaposhtani M AU - Mahdavi M TI - Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations JO - ChemistrySelect VL - 8 IS - 26 SP - EP - PY - 2023 ER -

Style

Citing Format

MLA

Gavanrudi MR, et al.. "Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations." ChemistrySelect, vol. 8, no. 26, 2023, pp. -.

APA

Gavanrudi MR, Halimi M, Najafzadehvarzi H, Alikhani M, Moazzam A, Farzipour S, Hosseini S, Mojtabavi S, Faramarzi MA, Nasliesfahani E, Mohammadikhanaposhtani M, Mahdavi M (2023). Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations. ChemistrySelect, 8(26), -.

Chicago

Gavanrudi MR, Halimi M, Najafzadehvarzi H, Alikhani M, Moazzam A, Farzipour S, Hosseini S, et al.. "Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations." ChemistrySelect 8, no. 26 (2023): -.

Harvard

Gavanrudi MR et al. (2023) 'Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations', ChemistrySelect, 8(26), pp. -.

Vancouver

Gavanrudi MR, Halimi M, Najafzadehvarzi H, Alikhani M, Moazzam A, Farzipour S, et al.. Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations. ChemistrySelect. 2023;8(26):-.

BibTex

@article{ author = {Gavanrudi MR and Halimi M and Najafzadehvarzi H and Alikhani M and Moazzam A and Farzipour S and Hosseini S and Mojtabavi S and Faramarzi MA and Nasliesfahani E and Mohammadikhanaposhtani M and Mahdavi M}, title = {Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations}, journal = {ChemistrySelect}, volume = {8}, number = {26}, pages = {-}, year = {2023} }

RIS

TY - JOUR
AU - Gavanrudi MR
AU - Halimi M
AU - Najafzadehvarzi H
AU - Alikhani M
AU - Moazzam A
AU - Farzipour S
AU - Hosseini S
AU - Mojtabavi S
AU - Faramarzi MA
AU - Nasliesfahani E
AU - Mohammadikhanaposhtani M
AU - Mahdavi M
TI - Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations
JO - ChemistrySelect
VL - 8
IS - 26
SP -
EP -
PY - 2023
ER -

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