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image of Design, Synthesis, Molecular Docking, and Antimicrobial Evaluation of Novel 1,3-thiazolidine-4-one Derivatives Incorporating Pyridine Scaffold

Abstract

Background

In this study, novel 1-(3-cyano-4,6-dimethyl-2-oxopyridin-1(2H)-yl)-3-phenylthiourea 2, 3-phenylthiazolidin-4-one 3, and arylidene-4-thiazolidinone derivatives 5a-k were synthesized in excellent yields. The produced compounds underwent assessment for their antimicrobial properties. Efficient and easy procedures for synthesizing arylidene-4-thiazolidinones 5a-k were delineated.

Materials and Methods

3-phenylthiazolidin-4-one 3 was achieved by reacting 1-(3-cyano-4,6-dimethyl-2-oxopyridin-1(2H)-yl)-3-phenylthiourea with ethyl 2-bromoacetate in EtOH, employing anhydrous sodium acetate at reflux temperature. Furthermore, a sequence of arylidene-4-thiazolidinone derivatives was synthesized by condensing 4-thiazolidinone 3 with different aromatic and heterocyclic aldehydes in a refluxing EtOH-containing piperidine. The binding mechanism of the thiazolidine derivatives to the dihydrofolate reductase (DHFR) and rhomboid protease proteins was determined by docking studies.

Results

Compounds , , , , and exhibited germicidal effects against both Gram-negative and Gram-positive bacteria. Furthermore, these compounds exhibited antifungal properties. The MIC ranged from 250 to below 500 μg/mL. The docking study revealed a strong correlation between the docking solutions and the experimental observations.

Conclusion

The structure of new compounds was identified by analytical and spectroscopic data. Certain thiazolidines showed exceptional antibacterial and antifungal properties. These interactions require more investigations that are comprehensive

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2025-11-03
2025-11-07

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Design, Synthesis, Molecular Docking, and Antimicrobial Evaluation of Novel 1,3-thiazolidine-4-one Derivatives Incorporating Pyridine Scaffold
Bentham Science Publishers ; https://doi.org/10.2174/0115701794363946250110025607
/content/journals/cos/10.2174/0115701794363946250110025607
/content/journals/cos/10.2174/0115701794363946250110025607
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  • Article Type:     Research Article
Keywords: pyridine ; Synthesis ; Molecular Docking ; 1,3-thiazolidine-4-one ; Antimicrobial activity

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