Synthesis of 2-thioxo-1,3-thiazolidin-4-one derivatives

Yarovenko, V. N.; Nikitina, A. S.; Заварзин, И. В.; Krayushkin, М. М.; Kovalenko, L. V.

doi:10.1007/s11172-007-0254-2

Cited by 11 publications

(2 citation statements)

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“…Many different conditions, catalysts and solvent were studied in this regard. Yarovenko et al [ 18 ] studied Knoevenagel condensation of rhodanine with various aldehydes in different solvents and with different catalysts. They found that methanol as a solvent and ethylenediammonium diacetate at ambient temperature gave high yield of the product, sodium acetate in acetic acid or acetic anhydride gave moderate yields, while ethanol and piperidine as a catalyst gave no product.…”

Section: Introductionmentioning

confidence: 99%

Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity

et al. 2018

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A series of rhodanine derivatives was synthesized in the Knoevenagel condensation of rhodanine and different aldehydes using choline chloride:urea (1:2) deep eutectic solvent. This environmentally friendly and catalyst free approach was very effective in the condensation of rhodanine with commercially available aldehydes, as well as the ones synthesized in our laboratory. All rhodanine derivatives were subjected to 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) scavenging activity investigation and quantitative structure-activity relationship (QSAR) studies were performed to elucidate their structure-activity relationship. The best multiple linear QSAR model demonstrate a stability in the internal validation and Y-randomization (R2 = 0.81; F = 24.225; Q2loo = 0.72; R2Yscr = 0.148). Sphericity of the molecule, ratio of symmetric atoms enhanced atomic mass along the principle axes in regard to total number of atoms in molecule, and 3D distribution of the atoms higher electronegativity (O, N, and S) in molecules are important characteristic for antioxidant ability of rhodanine derivatives. Molecular docking studies were carried out in order to explain in silico antioxidant studies, a specific protein tyrosine kinase (2HCK). The binding interactions of the most active compound have shown strong hydrogen bonding and van der Waals interactions with the target protein.

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Section: Introductionmentioning

confidence: 99%

Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity

et al. 2018

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“…The most common is Knoevenagel condensation between aromatic aldehydes and 4-thiazolidinones carried out in glacial acetic acid containing anhydrous sodium acetate (17Á 21). Instead of sodium acetate, acetic anhydride (22,23), ethanolamine (24,25), and ammonium chloride in ammonia (26Á28) have also been used. Moreover, other derivatives were prepared by condensation of 2-thioxo-4-thiazolidinone with pyridine aldehydes using glycine and sodium carbonate as catalysts (29).…”

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confidence: 99%