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

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 Publisher

Asgari MS¹ ; Tahmasebi B² ; Mojtabavi S³ ; Faramarzi MA³ ; Rahimi R⁴ ; Ranjbar PR¹ ; Biglar M² ; Larijani B² ; Rastegar H⁵ ; Mohammadikhanaposhtani M⁶ ; Mahdavi M²

Show Affiliations

1. School of Chemistry, College of Science, University of Tehran, Tehran, Iran
2. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
3. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
4. Department of Chemistry, Iran University of Science and Technology, Tehran, Iran
5. Cosmetic Products Research Center, Iranian Food and Drug Administration, MOHE, Tehran, Iran
6. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran

Source: Journal of Heterocyclic Chemistry Published:2020

Abstract

A new series of acridine-9-carboxamide-1,2,3-triazole derivatives 7a-m were designed, synthesized, and evaluated as novel α-glucosidase inhibitors. Acridine-9-carboxamide-1,2,3-triazole scaffold has been designed by combination of effective moieties from potent α-glucosidase inhibitors. Most of the synthesized compounds were more potent than standard inhibitor acarbose. Among the title compounds, the most potent compounds were compounds 7j, 7k, and 7a with IC50 values of 120.2 ± 1.0, 151.1 ± 1.4, and 157.6 ± 1.6 μM, respectively (IC50 value of acarbose = 750.0 ± 10.0 μM). Docking study of the most potent compounds demonstrated that these compounds formed stable complexes with α-glucosidase active site. Anti-α-amylase assay of compounds 7j, 7k, and 7a was performed and no activity was observed. in vitro cytotoxicity assay of the latter compounds revealed that these compounds were not cytotoxic toward human normal (HDF) and cancer (MCF-7) cell lines. ADME and toxicity prediction of compounds 7j, 7k, and 7a were also performed. © 2020 Wiley Periodicals LLC.

Style	Citing Format
MLA	Asgari MS, et al.. "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, vol. 57, no. 12, 2020, pp. 4348-4357.
APA	Asgari MS, Tahmasebi B, Mojtabavi S, Faramarzi MA, Rahimi R, Ranjbar PR, Biglar M, Larijani B, Rastegar H, Mohammadikhanaposhtani M, Mahdavi M (2020). 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, 57(12), 4348-4357.
Chicago	Asgari MS, Tahmasebi B, Mojtabavi S, Faramarzi MA, Rahimi R, Ranjbar PR, Biglar M, et al.. "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 57, no. 12 (2020): 4348-4357.
Harvard	Asgari MS et al. (2020) '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, 57(12), pp. 4348-4357.
Vancouver	Asgari MS, Tahmasebi B, Mojtabavi S, Faramarzi MA, Rahimi R, Ranjbar PR, et al.. 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;57(12):4348-4357.
BibTex	@article{ author = {Asgari MS and Tahmasebi B and Mojtabavi S and Faramarzi MA and Rahimi R and Ranjbar PR and Biglar M and Larijani B and Rastegar H and Mohammadikhanaposhtani M and Mahdavi M}, title = {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 = {Journal of Heterocyclic Chemistry}, volume = {57}, number = {12}, pages = {4348-4357}, year = {2020} }
RIS	TY - JOUR AU - Asgari MS AU - Tahmasebi B AU - Mojtabavi S AU - Faramarzi MA AU - Rahimi R AU - Ranjbar PR AU - Biglar M AU - Larijani B AU - Rastegar H AU - Mohammadikhanaposhtani M AU - Mahdavi M TI - 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 JO - Journal of Heterocyclic Chemistry VL - 57 IS - 12 SP - 4348 EP - 4357 PY - 2020 ER -

Style

Citing Format

MLA

Asgari MS, et al.. "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, vol. 57, no. 12, 2020, pp. 4348-4357.

APA

Asgari MS, Tahmasebi B, Mojtabavi S, Faramarzi MA, Rahimi R, Ranjbar PR, Biglar M, Larijani B, Rastegar H, Mohammadikhanaposhtani M, Mahdavi M (2020). 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, 57(12), 4348-4357.

Chicago

Asgari MS, Tahmasebi B, Mojtabavi S, Faramarzi MA, Rahimi R, Ranjbar PR, Biglar M, et al.. "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 57, no. 12 (2020): 4348-4357.

Harvard

Asgari MS et al. (2020) '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, 57(12), pp. 4348-4357.

Vancouver

Asgari MS, Tahmasebi B, Mojtabavi S, Faramarzi MA, Rahimi R, Ranjbar PR, et al.. 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;57(12):4348-4357.

BibTex

@article{ author = {Asgari MS and Tahmasebi B and Mojtabavi S and Faramarzi MA and Rahimi R and Ranjbar PR and Biglar M and Larijani B and Rastegar H and Mohammadikhanaposhtani M and Mahdavi M}, title = {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 = {Journal of Heterocyclic Chemistry}, volume = {57}, number = {12}, pages = {4348-4357}, year = {2020} }

RIS

TY - JOUR
AU - Asgari MS
AU - Tahmasebi B
AU - Mojtabavi S
AU - Faramarzi MA
AU - Rahimi R
AU - Ranjbar PR
AU - Biglar M
AU - Larijani B
AU - Rastegar H
AU - Mohammadikhanaposhtani M
AU - Mahdavi M
TI - 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
JO - Journal of Heterocyclic Chemistry
VL - 57
IS - 12
SP - 4348
EP - 4357
PY - 2020
ER -

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