Volume 29, Issue 182 (2-2020)                   J Mazandaran Univ Med Sci 2020, 29(182): 82-90 | Back to browse issues page

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Akhavan M, Foroughifar N, Pasdar H, Bekhradnia A. Green Chemical Synthesis and Biological Evaluation of Novel N-substituted Rhodanine Derivatives as Potential Antifungal Agents. J Mazandaran Univ Med Sci 2020; 29 (182) :82-90
URL: http://jmums.mazums.ac.ir/article-1-13967-en.html
Abstract:   (2314 Views)
Background and purpose: In medicinal chemistry, molecules containing rhodanine(2-thiazolidine-4-one) ring as a magic multifunctional privileged structural and functional scaffold show a broad range of potent pharmacological properties containing anti-microbial, antiviral, anti-diabetic, and anti-convulsant effects. Evidence suggests that the activity of the rhodanine derivative correlates with the size and the nature of the substituents at C-5 and N-3 positions. In this study, we synthesized new N-substituted rhodanine derivatives with arylidene substituent at the C-5 position via solvent-free Knoevenagel condensation reaction. We also investigated the antifungal activity of the compounds.
Materials and methods: A mixture of aromatic aldehyde (1 mmol) and rhodanin derivatives (1 mmol) was stirred in choline chloride (ChCl)/urea deep eutectic solvent (1 mL) at 100C in an oil bath for 1 hour. The progress of the reaction was monitored by TLC (2:1 n-hexane/ethyl acetate). Then, the crude compound was collected by vacuum filtration and washed using ice-cold solvent.
Results: Novel products were elucidated on the basis of elemental analyses as well as FTIR, Mass and 1H NMR, 13CNMR spectroscopy.
Conclusion: A green, comfortable and rapid procedure has been developed for the synthesis of N-substituted rhodanine derivatives using ChCl/Urea Deep Eutectic Ionic Liquid (DEILs) under solvent-free conditions.
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Type of Study: Research(Original) | Subject: Medicinal Chemistry

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