103788-60-9

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Thiazolidinedione, 5-[(4-hydroxyphenyl)methylene]is used as an inhibitor of angiogenesis for targeting VEGFR-2, which plays a crucial role in the development of new blood vessels in various diseases, including cancer. By inhibiting angiogenesis, 2,4-Thiazolidinedione, 5-[(4-hydroxyphenyl)methylene]- can potentially limit the growth and spread of tumors.
2,4-Thiazolidinedione, 5-[(4-hydroxyphenyl)methylene]is also used as an intermediate in the synthesis of MSDC 0602 (M755420), an analogue of thiazolidinediones. These compounds are effective insulin-sensitizing drugs, making them useful for treating various metabolic and inflammatory diseases, such as type 2 diabetes and obesity.
Additionally, due to their low affinity for binding and activation of peroxisome proliferator-activated receptor γ (PPARγ), these compounds can be further explored for their potential in developing new therapeutic strategies for a range of conditions related to insulin resistance and inflammation.

InChI:InChI=1S/C10H7NO3S/c12-7-3-1-6(2-4-7)5-8-9(13)11-10(14)15-8/h1-5,12H,(H,11,13,14)/b8-5+

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 123-08-0 4-hydroxy-benzaldehyde 
• 327055-07-2 ethyl 5-phenyl-2-(4-hydroxyphenylmethylene)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate 
• 123043-88-9 5-ethoxycarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione 
• 79-11-8 chloroacetic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 110-89-4 piperidine 

Downstream Products

• 74772-78-4 5-(4-hydroxybenzyl)-2,4-thiazolidinedione 
• 943447-75-4 C₁₈H₁₃NO₅S 
• 103788-51-8 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzylidene}-2,4-thiazolidinedione 
• 1020066-74-3 (Z)-5-(4-hydroxybenzylidene)-3-(1-methylcyclohexylmethyl)thiazolidine-2,4-dione 
• 1307299-63-3 (Z)-5-(4-hydroxybenzylidene)-3-[(7-hydroxy-2-oxo-2H-chromen-4-yl)methyl]thiazolidine-2,4-dione 
• 1228763-97-0 (Z)-2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)-N-(5-nitrothiazol-2-yl)acetamide 
• 1228763-96-9 (Z)-5-(2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)acetyl)-2-hydroxybenzamide 

Relevant academic research and scientific papers

Effect of thiazolidinedione phenylacetate derivatives on wound-healing activity

The aim of this work was to evaluate the synthesis and structure–activity relationship of 4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl 2-phenylacetate derivatives as potential wound-healing agents. The IC50 values of the lead compounds rang

Design and synthesis of novel pyranone-based insulin sensitizers exhibiting in vivo hepatoprotective activity

Serious hepatic and cardiovascular complications after treatment with the thiazolidinedione (TZD) class of insulin sensitizers have significantly retarded the advancement of new TZD-based peroxisome proliferator-activated receptor agonists that bind with high affinity and selectivity. The aim of the present study is to design new antihyperglycemic agents that promote insulin sensitivity through partial adipogenesis as well as demonstrate beneficial hepatoprotective activity. The results indicated that among forty screened compounds, three of the novel pyranones at a dose of 10 μM increased the preadipocyte differentiation into adipocytes in 3T3-L1 cell lines. They showed an insulin-sensitizing effect by significantly increasing the glucose uptake and exhibited insulin resistance reversal. These compounds at a dose of 20 mg kg-1 significantly protected against thioacetamide-induced hepatotoxic changes in the serum biochemistry as compared to standard hepatoprotectant silymarin and also ameliorated the histopathological alterations in the liver tissues after acute liver injury in Swiss mice.

Synthesis of 5-arylidene-2,4-thiazolidinediones by Knoevenagel condensation catalyzed by baker's yeast

An ecofriendly baker's yeast catalyzed Knoevenagel condensation of aromatic aldehydes and active methylene compounds has been performed. The developed protocol has been found to be applicable for obtaining 5-arylidene-2,4- thiazolidinediones, the precursors of hypoglycemic agents. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2011.

A simple, efficient and green procedure for knoevenagel condensation in hydroxy-functionalized ionic liquids

An efficient and simple Knoevenagel condensation catalyzed by hydroxy-functionalized ionic liquids proceeded smoothly in high yields under ambient and solvent-free conditions. The condensation procedures of aryl aldehydes and 2,4-thiazolidinedione was involved in hydrogen bonding interactions between the hydroxy groups of the ILs and the carbonyl group of the aldehyde. The ionic liquids can be reused for five times without significant loss in activity.

De-novo design and synthesis of conformationally restricted thiazolidine-2,4-dione analogues: highly selective PPAR-γ agonist in search of anti-diabetic agent

In the present investigation, design, molecular docking simulations, and synthesis of few 2,4-thiazolidinedione for selective modulation of PPAR-gamma are reported. Further evaluation of anti-diabetic activity of few thiazolidine-2,4-diones is assessed using cell line analysis. The structures of the synthesized compounds were confirmed on the basis of FT-IR, 1H-NMR, and mass analyses. Acute toxicity study was done to by using Trypan blue assay and MTT assay of the synthesized compounds. Synthesized compounds were evaluated for their antihyperglycemic effect by glucose absorption assay. The compound code TZD4 showed highest percentage of glucose absorption by 3T3-L1 cells compared with control.

Design, synthesis, molecular docking, and in vitro antidiabetic activity of novel PPARγ agonist

Abstract: The present work describes the design, synthesis, molecular docking, biological evaluation, and assessment of structure–activity relationship of new derivatives based upon the molecular skeleton of the drug pioglitazone, a compound which is currently used for the management of type 2 diabetes mellitus. Pioglitazone has several side effects such as weight gain, edema, congestive heart failure, and bladder cancer. Therefore, there is a strong demand for identification of new lead candidates in the treatment of type 2 diabetes mellitus. A series of 24 compounds were prepared and evaluated for their peroxisome proliferator-activated receptor-γ (PPARγ) binding affinity assay and the IC50 values were determined. Among these compounds, six compounds exhibited promising IC50 values as compared to standard drugs pioglitazone and rosiglitazone. Furthermore, in order to confirm the target of these molecules, molecular docking study was carried out with peroxisome proliferator-activated receptor-γ (PPARγ) protein. Molecular modeling studies suggested that these compounds appropriately interact in the active sites of receptor. Graphical abstract: [Figure not available: see fulltext.].

5-Benzylidene-2,4-thiazolidenedione derivatives: Design, synthesis and evaluation as inhibitors of angiogenesis targeting VEGR-2

A series of novel 5-benzylidene-2,4-thiazolidinediones were designed as inhibitors of angiogenesis targeting VEGFR-2. In docking study, molecules showed similar way of binding with VEGFR-2 as that of the co-crystallized ligand. Compounds were then synthes

Solid acid TS-1 catalyst: an efficient catalyst in Knoevenagel condensation for the synthesis of 5-arylidene-2,4-thiazolidinediones/Rhodanines in aqueous medium

Abstract: TS-1 zeolite was prepared for the synthesis of 5-arylidene-2,4-thiazolidinediones/Rhodanines in aqueous medium by incorporating titanium(IV) cations in a silicate-1 framework using hydrothermal treatment and characterized by using XRD, EDX, BET, FT-IR and SEM techniques. The catalytic activity of the catalyst was tested for Knoevenagel condensation reaction. The condensation of active ethylene 2,4-thiazolidinedione with substituted aryl aldehydes under aqueous medium at 90?°C afforded the corresponding product in excellent yield up to 92% within 30?min. The present method offers several advantages over the reported methods such as easy separation of catalyst, simple work-up procedure, and an excellent yield of desired product. Furthermore, the catalyst could be reused without significant loss in activity. Graphical abstract: [Figure not available: see fulltext.]

A novel chrysin thiazole derivative polarizes macrophages to an M1 phenotype via targeting TLR4

Tumor-associated macrophages (TAMs) are an important cause of tumorigenesis and tumor development. M2 macrophages can promote tumor growth while M1 macrophages kill tumor cells, therefore, polarizing macrophages to achieve a functional M1 phenotype could effectively play its anti-tumor role. In the current study, we synthesized a novel chrysin derivative which is termed as ChR-TD. And we found ChR-TD might be a ligand of TLR4 that polarized the TAMs towards M1 phenotype and played its anti-tumor role. Further study indicated that ChR-TD reprogrammed the macrophages into an M1 phenotype via TLR4 activation. Moreover, ChR-TD activated TLR4/NF-κB signaling pathway and promoted the NF-κB/p65 translocated into the nuclear, leading to the activation of NF-κB and proinflammatory cytokines release. In addition, type I interferon signaling was also activated by ChR-TD, leading to the expressions of IFN-α and IFN-β and its targeted genes NOS2, MCP-1 and IP-10 were significantly increased in macrophages. Importantly, these effects were disturbed in TLR4?/? macrophages, which are constructed by using CRISPR/Cas9 system. And the molecule docking simulation further indicated that ChR-TD could bind to TLR4 and might be a ligand of TLR4. Hence, these findings suggested that ChR-TD might be a ligand of TLR4 and can be used as a potential lead compound for tumors treatment.

Copper(II)-complex functionalized magnetite nanoparticles: a highly efficient heterogeneous nanocatalyst for the synthesis of 5-arylidenthiazolidine-2,4-diones and 5-arylidene-2-thioxothiazolidin-4-one

Abstract: Magnetite nanoparticles (MNPs) have proved to be a useful support for heterogeneous catalysis. We have synthesized Fe3O4 MNPs functionalized with a copper(II) complex, and tested the resulting material as a heterogeneous nanocatalyst. The catalyst was tested for aldol condensation reactions between aliphatic/aromatic aldehydes and rhodanine or thiazolidine-2,4-dione (TZD) derivatives under reflux in ethanol, giving the target products in high yield. Environmentally benign chemistry, short reaction times, simple work-up, excellent yields, and the reusability of the new nanocatalyst are beneficial features of the present study. The nanocatalyst was characterized by scanning electron microscopy, vibrating sample magnetometery, thermogravimetry, X-ray diffraction, and energy-dispersive X-ray analyses. The data showed that the magnetic nanoparticles are super-paramagnetic with a size range of 10–20?nm. Graphical Abstract: [Figure not available: see fulltext.].