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Comb Chem High Throughput Screen. 2019 Nov 26. doi: 10.2174/1386207322666191127103122. [Epub ahead of print]

Green synthesis, biological activity evaluation, and molecular docking studies of aryl alkylidene 2, 4-thiazolidinedione and rhodanine derivatives as antimicrobial agents.

Author information

1
Department of Chemistry, Tehran North Branch, Islamic Azad University, Tehran, Iran.
2
Pharmaceutical Sciences Research Center, Department of Medicinal Chemistry, Mazandaran University of Medical Sciences, Sari, Iran.

Abstract

AIM AND OBJECTIVE:

The magic scaffolds rhodanine and thiazolidine are very important heterocyclic compounds in drug design and discovery. their multi-functional and broad spectrum derivatives are antibacterial, antifungal, antiviral, antimalarial, anti-inflammatory. These agents often exhibiting selective toxicity. The goal of this study was molecular docking, green and solvent-free efficient synthesis of a new series of hetero/aromatic substituted rhodanine and thiazolidine analogues and then investigating their antimicrobial activity.

MATERIALS AND METHODS:

To a mixture of TZD or rhodanine (1 mmol) in the presence of ionic liquid ChCl/urea various aldehyde (1 mmol) was added and After completion of the reaction, obtained crude compound was collected by filtration and products were recrystallized from ethanol. The binding-free energy between All synthesized compounds with 3EEJ protein (C. glabrata enzyme) were obtained by molecular docking studies. These compounds were evaluated using micro-dilution method against (ATCC 6538) and (ATCC 12228) Gram-negative, (ATCC 8739) and (ATCC 9027) as Gram-positive and (ATCC 1012), (ATCC 339), C. (ATCC 1057), (ATCC 503), (ATCC 340) and (ATCC 194) as fungi.

RESULTS:

All of the acceptable products were determined by 1H NMR, 13C NMR, Mas and FT-IR spectroscopy. The binding-free energy between compounds 10a and 10b with 3EEJ protein were found to be -8.08 kcal/mol and -8.15 kcal/mol respectively. These compounds having heteroaromatic ring attached to the TZD or rhodanine core showed excellent antimicrobial activity with MIC values of 0.25-8 µg/mL (compound 10a) and 0.5-16 µg/mL (compound 10b) against the most tested fungi strains, Gram-positive and Gram-negative bacteria.

CONCLUSION:

A convenient and rapid method has been developed for the synthesis of rhodanine and thiazolidine-2,4-dione (TZD) derivatives as efficient antimicrobial agents using a Deep Eutectic Ionic Liquids (DEILs) choline chloride urea under solvent-free condition. among of all newly synthesized compounds, (Z)-5-((quinoxalin-3-yl) methylene) thiazolidine-2, 4-dione (10a) and (Z)-5- ((quinoxalin-3-yl) methylene)-2-thioxothiazolidin-one (10b) exerted the promising effect and these compounds can be considered to be further probed as inhibitors of cgDHFR enzyme.

KEYWORDS:

Antimicrobial activity; Deep Eutectic Solvents (DESs); Molecular docking studies; Rhodanine; Solvent-free conditions; Thiazolidine

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