New thioureas based on thiazolidines with antioxidant potential

Silva, Tiago Lima da; Miolo, Laura Maria Forain; Sousa, Fernanda Severo Sabedra; Brod, Lucimar M. Pinto; Savegnago, Lucielli; Schneider, Paulo H.

doi:10.1016/j.tetlet.2015.10.037

Cited by 28 publications

(24 citation statements)

References 123 publications

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“…In principle, it is possible to preserve the original skeleton and replace groups attached to the nitrogen atom(s), changing the substitution pattern. For example, the thiazolidine motif was introduced via the reaction of mono-aryl-substituted thioureas and the appropriate carboxylic acids with boronic acid catalyst (Scheme 19) [87]. Various prepared N-acyl derivatives included chiral ones and were found to exhibit antioxidant activity.…”

Section: Preparation Of Chiral Thioureas From Other Thioureasmentioning

confidence: 99%

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Chiral Thioureas—Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry

et al. 2020

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For almost 20 years, thioureas have been experiencing a renaissance of interest with the emerged development of asymmetric organocatalysts. Due to their relatively high acidity and strong hydrogen bond donor capability, they differ significantly from ureas and offer, appropriately modified, great potential as organocatalysts, chelators, drug candidates, etc. The review focuses on the family of chiral thioureas, presenting an overview of the current state of knowledge on their synthesis and selected applications in stereoselective synthesis and drug development.

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Section: Preparation Of Chiral Thioureas From Other Thioureasmentioning

confidence: 99%

“…Scheme 19. Reaction of monosubstituted thiourea with a chiral carboxylic acid as a route to a chiral thiourea [87].…”

Section: Preparation Of Chiral Thioureas From Other Thioureasmentioning

confidence: 99%

Chiral Thioureas—Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry

et al. 2020

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“…However, they were not used as organocatalyst, but were tested for their antioxidant activity. [31] Therefore, we decided to synthetize new thioureas derived from thiazolidine 4 to test in asymmetric aldol reactions.…”

Section: Scheme 1 Synthesis Of Organocatalysts 3a-6amentioning

confidence: 99%

Chiral Thiazolidine based Organocatalysts: Synthesis and Application in Asymmetric Aldol Reactions

Félix

Simões

Sousa

et al. 2020

LOC

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Several novel chiral organocatalysts derived from thiazolidines containing amide and thioureia functionalities were synthesized in good yields. These organocatalysts were tested in the asymmetric aldol reaction of acetone with p-nitrobenzaldehyde. Reaction parameters such as reaction time, catalyst loading and solvent were optimized. Products with conversions up to 84% and enantiomeric ratios (er) up to 84.5:15.5 (R:S) were obtained. The effect of several chiral and non-chiral additives on the reactivity and selectivity of the reaction was also evaluated. The reaction was extended to other aromatic aldehydes with the best organocatalyst and when p-bromobenzaldehyde was used, an er of 94.5:5.5 (R:S) was obtained.

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“…Thiazolidinones are important pharmaceutical compounds because of their biological activities, such as anti‐inflammatory, [ 22 ] antifungal, [ 23 ] antimalarial, [ 24 ] anticancer, [ 25,26 ] antitumor, [ 27,28 ] antimicrobial, [ 29 ] antiviral, [ 30 ] herbicidal, [ 31 ] antiproliferative [ 32 ] and anti‐ Toxoplasma gondii activities. [ 33 ] Furthermore, they are cycloxygenase inhibitors, [ 34 ] anti‐HIV, [ 35 ] anticonvulsants, [ 36 ] Ca 2+ channel blockers, [ 37 ] antioxidants, [ 38,39 ] antihistaminic, [ 40 ] an antiplatelet activating factor, [ 41 ] antitubercular, [ 42 ] and analgesic. [ 43 ]…”

Section: Introductionmentioning

confidence: 99%

Copper/Schiff‐base complex immobilized on amine functionalized silica mesoporous magnetic nanoparticles under solvent‐free condition: A facile and new avenue for the synthesis of thiazolidin‐4‐ones

Fekri

Zeinali²

2020

Applied Organom Chemis

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A copper/Schiff‐base complex supported on amine‐functionalized silica mesoporous magnetic nanoparticles was prepared as novel magnetically interphase nanoparticles and its morphology and structure were evaluated using Fourier transform infrared spectroscopy, X‐ray diffraction, field emission scanning electron microscopy, transmission electron microscopy, energy dispersive X‐ray spectroscopy, thermogravimetric analysis, zeta potential, and a vibrating sample magnetometer. The catalytic activity of the synthesized nanoparticles was evaluated for the synthesis of thiazolidine‐4‐ones.

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New thioureas based on thiazolidines with antioxidant potential

Cited by 28 publications

References 123 publications

Chiral Thioureas—Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry

Chiral Thioureas—Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry

Chiral Thiazolidine based Organocatalysts: Synthesis and Application in Asymmetric Aldol Reactions

Copper/Schiff‐base complex immobilized on amine functionalized silica mesoporous magnetic nanoparticles under solvent‐free condition: A facile and new avenue for the synthesis of thiazolidin‐4‐ones

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