Open Chemistry Journal




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RESEARCH ARTICLE

Synthesis, α-Amylase Inhibitory Activity and Molecular Docking Studies of 2,4-Thiazolidinedione Derivatives



Fawad Naeem1, Humaira Nadeem2, *, Aun Muhammad3, Muhammad Ammar Zahid1, Adil Saeed2
1 Department of Pharmaceutical Chemistry, Shifa Tameer-e-Millat University, Islamabad, Pakistan
2 Department of Pharmaceutical Chemistry, Riphah Institute of Pharmaceutical Sciences, G-7/4, Islamabad, Pakistan
3 Department of Biotechnology, Institute of Molecular Biology and Biotechnology, Bahauddin Zikariya University, Multan, Pakistan

Abstract

Introduction:

2,4-Thiazolidinedione and its derivatives exhibit a variety of pharmacological activities including antidiabetic, antiviral, antifungal, anti-inflammatory, anti-cancer and aldose reductase inhibitory activities. Keeping in mind the pharmacological potential of 2,4-Thiazolidinedione derivatives as antidiabetic agents, seven arylidene derivatives of 2,4-thiazolidinedione 1(a-g) and four corresponding acetic acid derivatives 2(a-d) have been synthesized by a three-step procedure.

Methods:

All the synthesized compounds were characterized by elemental analysis, FTIR, 1HNMR, and 13CNMR and further screened for their α-amylase inhibitory potential.

Results:

All the compounds 1(a-g) and 2(a-d) showed varying degree of α-amylase inhibition, especially compound 1c (IC50 = 6.59μg/ml), 1d (IC50=2.03μg/ml) and 1g (IC50 = 3.14μg/ml) displayed significantly potent α-amylase inhibition as compared to the standard acarbose (IC50 = 8.26μg/ml). None of the acetic acid derivatives of 5-arylidene-2,4-thiazolidinedione showed prominent inhibitory activity. Docking results indicated that the best binding conformation was found inside the active site cleft of enzyme responsible for hydrolysis of carbohydrates.

Conclusion:

Therefore, it can be concluded that 2,4-thiazolidinedione derivatives can be used as effective lead molecules for the development of α-amylase inhibitors for the management of diabetes.

Keywords: Thiazolidinedione, Arylidene, Derivatives, Postprandial, Hyperglycaemia, α-amylase inhibition, Anti-diabetic, In-silico docking.


Article Information


Identifiers and Pagination:

Year: 2018
Volume: 5
First Page: 134
Last Page: 144
Publisher Id: CHEM-5-134
DOI: 10.2174/1874842201805010134

Article History:

Received Date: 19/5/2018
Revision Received Date: 11/10/2018
Acceptance Date: 21/10/2018
Electronic publication date: 30/11/2018
Collection year: 2018

© 2018 Nadeem et al.

open-access license: This is an open access article distributed under the terms of the Creative Commons Attribution 4.0 International Public License (CC-BY 4.0), a copy of which is available at: https://creativecommons.org/licenses/by/4.0/legalcode. This license permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.


* Address correspondence to this author at the Riphah Institute of Pharmaceutical Sciences, G-7/4, Islamabad, Pakistan; Tel: 03235010850; E-mail: humaira.nadeem@riphah.edu.pk



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