80353-43-1

Usage

Uses

Used in Pharmaceutical Development:
3-Benzyl-2-phenyl-1,3-thiazolidin-4-one is used as a pharmaceutical candidate for its diverse biological activities, including anti-inflammatory, antioxidant, and antitumor properties.
Used in Anti-inflammatory Applications:
3-Benzzyl-2-phenyl-1,3-thiazolidin-4-one is used as an anti-inflammatory agent, potentially helping to reduce inflammation and alleviate symptoms associated with various inflammatory conditions.
Used in Antioxidant Applications:
3-Benzyl-2-phenyl-1,3-thiazolidin-4-one is used as an antioxidant, potentially protecting cells from oxidative stress and damage, which can contribute to various diseases and aging.
Used in Antitumor Applications:
3-Benzyl-2-phenyl-1,3-thiazolidin-4-one is used as an antitumor agent, potentially inhibiting the growth and spread of cancer cells.
Used in Diabetes and Insulin Resistance Treatment:
3-Benzyl-2-phenyl-1,3-thiazolidin-4-one is used as a treatment for diabetes and insulin resistance, potentially helping to improve blood sugar control and reduce the risk of complications associated with these conditions.
Used in Neurodegenerative Disease Treatment:
3-Benzyl-2-phenyl-1,3-thiazolidin-4-one is used in the treatment of neurodegenerative diseases such as Alzheimer's and Parkinson's, potentially slowing the progression of these diseases and improving the quality of life for affected individuals.

Upstream product

• 100-52-7 benzaldehyde 
• 68-11-1 mercaptoacetic acid 
• 100-46-9 benzylamine 
• 80353-48-6 N-Benzyl-2-[(benzylcarbamoyl-methylsulfanyl)-phenyl-methylsulfanyl]-acetamide 
• 780-25-6 N-benzylidene benzylamine 
• 622-79-7 benzyl azide 

Downstream Products

• 141727-37-9 3-Benzyl-5-fluoro-2-phenyl-thiazolidin-4-one 
• 141727-43-7 3-Benzyl-5-fluoro-1,1-dioxo-2-phenyl-1λ⁶-thiazolidin-4-one 
• 141727-48-2 (3S,4S)/(3R,4R)-1-benzyl-3-fluoro-4-phenylazetidin-2-one 
• 141727-48-2 (3R,4S)/(3S,4R)-1-benzyl-3-fluoro-4-phenylazetidin-2-one 

Relevant academic research and scientific papers

An unexpected formation of 2-aryl-3-benzyl-1,3-thiazolidin-4-ones

The reactions of L-valine, arenealdehydes, mercaptoacetic acid and DIPEA produce 2-aryl-3-benzyl-1,3-thiazolidin-4-ones with moderate yields (48-65%). Characterization of the 1,3-thiazolidin-4-ones was achieved by NMR and confirmed by X-ray crystallograph

Visible-light-driven photocatalytic activity of ZnO/g-C3N4 heterojunction for the green synthesis of biologically interest small molecules of thiazolidinones

Designing a photocatalytic system with complementary properties including high surface area, high loading, extraordinary electronic properties, and easy separation for increases photocatalytic performance has remained a challenge in photocatalytic applications. Herein, an environmentally benign approach was developed to fabricate graphitic carbon nitride (g-C3N4) decorated with nanorods zinc oxide (ZnO). The photocatalytic activity of ZnO decorated on the g-C3N4 surface was developed in the synthesis of 1,3-thiazolidin-4-ones and bis-thiazolidinones under very mild and sustainable reaction conditions. The reaction can be carried out by utilizing visible light without the requirement of any additive and other external sources of energy. It was found that the proposed photocatalyst is a more facile, recyclable, large-scale application and provides some new insights into the stabilization of semiconductors for a variety of applications.

Sonochemical Green Synthesis of Yttrium Oxide (Y2O3) Nanoparticles as a Novel Heterogeneous Catalyst for the Construction of Biologically Interesting 1,3-Thiazolidin-4-ones

Abstract: This paper describes a facile and green strategy for the synthesis of yttrium oxide nanoparticles (Y2O3 NPs) by a straightforward process using Liriope platyphylla rhizome extract as the reducing agent and yttrium nitrate hexahydrate as the sole precursor without other additives. The crystallinity, surface chemistry, morphology, elemental composition, and thermal properties of the synthesized NPs are thoroughly investigated. The synthesized NPs shows remarkable catalytic activity for the construction of biologically interesting 1,3-thiazolidin-4-ones. Graphical Abstract: [Figure not available: see fulltext.].

A catalysis study of mesoporous MCM-41 supported Schiff base and CuSO4·5H2O in a highly regioselective synthesis of 4-thiazolidinone derivatives from cyclocondensation of mercaptoacetic acid

Mesoporous MCM-41 supported Schiff base and CuSO4·5H2O shows high catalytic activity in the cyclocondensation of mercaptoacetic acid with imines (or aldehydes and amines) to afford pharmaceutically important thiazolidinone derivatives. The catalytic reactions involving two-components or three-components afforded the desired product in high yields (up to 98% and 99%). Moreover, the catalyst works well with respect to recyclability, giving the product in 85% and 83% yields after recycling six times.

Catalyst-free and environment friendly synthesis of 2-aryl-3-substituted-4-thiazolidinones in water

A simple, efficient, eco-friendly, and cost-effective method has been developed for the three component one pot synthesis of 2-aryl-3-substituted-4-thiazolidinones is described. The method provides rapid and easy access to thiazolidinone compounds in good to excellent yields.

A facile and effective procedure for the synthesis of 4-thiazolidinone derivatives using Y(OTf)3 as catalyst

ABSTRACT: A one-pot three-component reaction for the synthesis of 4-thiazolidinone derivatives has been established by reacting readily available and inexpensive starting materials of amines, aldehydes and thioglycolic acid using Y(OTf)3 (5 mol%) as catalyst in tetrahydrofuran. This method is very efficient due to low catalyst loading and mild reaction conditions and provides an efficient and promising synthetic strategy for the construction of the thiazolidinone skeleton.

Silica gel promoted environment-friendly synthesis of 2,3-disubstituted 4-thiazolidinones

Three-component one pot silica gel promoted synthesis of 2,3-disubstituted 4-thiazolidinones is described. The method provides rapid and easy access to thiazolidinone compounds in good to excellent yields.

The first solvent-free, microwave-accelerated, three-component synthesis of thiazolidin-4-ones via one-pot tandem Staudinger/aza-wittig reaction

An efficient and rapid, solvent-free, microwave-accelerated, one-pot, three-component protocol for thiazolidin-4-ones synthesis from organic azides has been reported for the first time via Staudinger/aza-Wittig reaction. The microwave-accelerated, solvent-free approach overcomes the limitations associated with the prevailing solution phase methodologies. In particular, its novelty is that it eradicates the vital limitation, that is, accumulation of water (byproduct) that is known to affect the yield and rate of the reaction. Thus, a library of thiazolidin-4-ones has been synthesized in short time in excellent yields (92-96%).

Supported protic acid-catalyzed synthesis of 2,3-disubstituted thiazolidin-4-ones: Enhancement of the catalytic potential of protic acid by adsorption on solid supports

The catalytic potential of various protic acids has been assessed for the one pot tandem condensation-cyclisation reaction involving an aldehyde, an amine, and thioglycolic acid to form 2,3-disubstituted thiazolidin-4-ones. The catalytic potential of the various protic acids that follows the order TfOH > HClO4 > H2SO4 ～ p-TsOH > MsOH ～ HBF4 > TFA ～ AcOH is improved significantly by adsorption on solid supports, in particular using silica gel (230-400 mesh size), with the resulting relative catalytic potential following the order HClO 4-SiO2 > TfOH-SiO2 ? H2SO 4-SiO2 > p-TsOH-SiO2 > MsOH-SiO 2 ～ HBF4-SiO2 > TFA-SiO2 ～ HOAc-SiO2. The better catalytic potential of HClO 4-SiO2 as compared to that of Tf-SiO2, although TfOH is a stronger protic acid than HClO4, can be rationalised through a transition state model depicting the interaction of the individual protic acid with SiO2. The catalytic efficiency of HClO4 adsorbed on various solid supports was in the order HClO4-SiO 2 ? HClO4-K10 > HClO4-KSF > HClO 4-TiO2 ～ HClO4-Al2O3. The catalytic system HClO4-SiO2 is compatible with different variations of aldehydes (aryl/heteroaryl/alkyl/cycloalkyl) and the amines (aryl/heteroaryl/arylalkyl/alkyl/cycloalkyl) affording the desired 2,3-disubstituted thiazolidin-4-ones in 70-87% yields (43 examples). The electronic and the steric factors associated with the aldehydes and the amines provide a handle for selective thiazolidinone formation and were found to be dependent on the extent of imine formation. No significant amount of thiazolidinone formation took place during the reaction of the preformed amide (synthesised from the amine and thioglycolic acid) with benzaldehyde suggesting that the reaction proceeds through the initial reversible imine formation followed by cyclocondensation of the preformed imine with thioglycolic acid, the reversible imine formation being the determining step to control selectivity of thiazolidinone formation in competitive environments. The feasibility of a large scale reaction and catalyst recycling/reuse is demonstrated.

Carbodiimide mediated synthesis of 4-thiazolidinones by one-pot three-component condensation

In the present study, 4-thiazolidinones have been assembled by DCC mediated three-component reaction of amine, aldehyde and mercaptoacetic acid. The final compounds are obtained in quantitative yields within one hour.