Abstract
BackgroundLooking at the extensive biological potential of thiazolidine-2,4-dione (TZD) moiety, a new series of thiazolidine-2,4-dione analogues was synthesized. Different spectral techniques (1H-NMR, IR, MS etc.) were used to confirm the chemical structures of the synthesized analogues. These synthesized compounds were screened for their antioxidant and antimicrobial potential.Results and discussionThe antimicrobial screening was carried out against selected strains of fungi and bacteria using serial tube dilution method. The antioxidant potential was assessed using stable 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging method. Further, the interaction between synthesized thiazolidine-2,4-dione compounds and DNA gyrase was explored using molecular docking studies. Various ADME parameters were also studied to evaluate the drug likeness of the synthesized compounds.ConclusionIn antimicrobial evaluation, the compounds 4, 9, 11, 12, 13, 15 and 16 displayed promising activity against selected strains of microbes. Antioxidant evaluation found compound 6 having IC50 = 9.18 μg/mL to be the most potent compound in the series. The molecular docking study revealed compounds 4 (dock score = − 4.73) and 7 (dock score = − 4.61) with decent docking score, possess good interaction inside the ATP binding pocket of DNA gyrase and therefore can be used as lead structure for further optimizing into potent antimicrobial molecule.
Highlights
The increasing rate of microbial infection and development of drug resistance amongst different microbial strains are the major cause of worry for human life worldwide [1]
DNA (Deoxyribonucleic acid) gyrase is a vital enzyme of topoisomerases class that are involved in the regulation of topological transitions of DNA by the formation of negative supercoils
The 1H-NMR spectra designated that the presence of multiplet signals between 6.52 and 8.28 δ ppm reflected the presence of aromatic protons in synthesized molecules
Summary
Chemistry The synthesis of TZD derivatives (1–20) were accomplished using the synthetic route depicted in Scheme 1. °C: 130–132; Rf value: 0.77a; % yield: 75; IR (KBr c m−1): 3444.26 (N–H str., thiazolidine ring), 1743.88 (C=O str., thiazolidin-2,4-dione ring), 1702.79 (C=N str., imine group), 1505.14 (C=C str., aromatic ring), 1614.33 (C=C str., methylene group), 3065.92 (C–H str., aromatic ring), 2926.15 (C–H str., aliphatic), 1291.79 (C–N str., thiazolidine ring), 606.22 (C–S bend., thiazolidine ring), 1155.22 (C–C str.), 1024.26 (O–CH3 str., o-substitution on phenyl ring); 1H NMR (δ, DMSO): 6.98–8.04 (m, 8H, Ar–H), 7.78 (s, 1H, –CH=), 8.71 (s, 1H, CH=N), 12.42 (s, 1H, NH), 3.78(s, 3H, OCH3); M. These molecules may further be used as lead compounds to derive more potent and less toxic novel antioxidant and antimicrobial agents
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