Author:
Kumar Harsh,Deep Aakash,Marwaha Rakesh Kumar
Abstract
Abstract
Background
Looking 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 discussion
The 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.
Conclusion
In 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.
Publisher
Springer Science and Business Media LLC
Reference31 articles.
1. Prasad D, Kumar A, Shukla PK, Nath M (2011) Design, synthesis and antimicrobial evaluation of novel 2-aryl-thiazolidin-4-one derivatives. Org Med Chem Lett 1:4–11
2. Moorthy P, Ekambaram SP, Perumal SS (2019) Synthesis, characterization and antimicrobial evaluation of imidazolyl thiazolidinedione derivatives. Arab J Chem 12(3):413–419
3. Keche AP, Hatnapure GD, Tale RH, Rodge AH, Birajdar SS, Kamble VM (2012) Novel pyrimidine derivatives with aryl urea, thiourea and sulfonamide moieties: synthesis, anti-infammatory and antimicrobial evaluation. Bioorg Med Chem Lett 22(10):3445–3448
4. Parekh NM, Juddhawala KV, Rawal BM (2013) Antimicrobial activity of thiazolyl benzene sulfonamide-condensed 2,4-thiazolidinediones derivatives. Med Chem Res 22:2737–2745
5. Desai NC, Satodiya HM, Rajpara KM, Joshi VV, Bhatt K, Vaghani HV (2014) Synthesis and evaluation of N-substituted thiazolidine-2,4-dione containing pyrazole as potent antimicrobial agents. Antiinfect Agents 12:85–94
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