CAS 103788-60-9

2,4-Thiazolidinedione, 5-[(4-hydroxyphenyl)methylene]-

Description:

2,4-Thiazolidinedione, 5-[(4-hydroxyphenyl)methylene]- is a chemical compound characterized by its thiazolidinedione core, which features a five-membered ring containing both sulfur and nitrogen atoms. This compound is known for its potential biological activity, particularly in the context of diabetes research, as thiazolidinediones are often studied for their insulin-sensitizing properties. The presence of the 4-hydroxyphenylmethylene group suggests that it may exhibit additional pharmacological effects due to the phenolic structure, which can influence its reactivity and interaction with biological targets. The compound's molecular structure contributes to its solubility and stability, which are important factors in its potential applications. Furthermore, the compound may exhibit antioxidant properties due to the hydroxyl group, making it of interest in various fields, including medicinal chemistry and drug development. As with many thiazolidinediones, understanding its mechanism of action and potential side effects is crucial for evaluating its therapeutic potential.

Formula: C₁₀H₇NO₃S

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+

InChI key: InChIKey=ARHIHDVVUHVQCP-UHFFFAOYSA-N

SMILES: C(=C1SC(=O)NC1=O)C2=CC=C(O)C=C2

Synonyms:

• 2,4-Thiazolidinedione, 5-[(4-hydroxyphenyl)methylene]-
• 5-[(4-Hydroxyphenyl)methylene]-2,4-thiazolidinedione
• (Z)-5-(4-hydroxybenzylidene)thiazolidine-2,4-dione(WX180325)
• (Z)-5-(4-hydroxybenzylidene)thiazolidine-2,4-dione
• 5-(4-hydroxybenzylidene)-2,4-thiazolidinedione

5-(4-Hydroxybenzylidene)thiazolidine-2,4-dione

CAS: 103788-60-9

Formula: C₁₀H₇NO₃S

Purity: %

Molecular weight: 221.2325

Ref: IN-DA00976U

(5E)-5-(4-Hydroxybenzylidene)-1,3-thiazolidine-2,4-dione

Controlled Product

CAS: 103788-60-9

Applications 5-[(4-Hydroxyphenyl)methylene]-2,4-thiazolidinedione is a 5-Benzylidene-2,4-thiazolidenedione derivative designed as inhibitors of angiogenesis targeting VEGFR-2. Also, it is an intermediate used in the synthesis of MSDC 0602 (M755420), which is an analogue of thiazolidinediones, exhibits low affinity for binding and activation of peroxisome proliferator-activated receptor γ (PPARγ). Thiazolidinediones are effective insulin-sensitizing drugs for treating various metabolic and inflammatory diseases.
References Bhanushali, U., et al.: Bioorg. Chem., 67, 139-147 (2016); Chen, Z., et al.: J. Biol. Chem. 287, 23537 (2012); Fukunaga, T., et al.: J. Bone Miner. Res., 30, 508 (2015)

Formula: C₁₀H₇NO₃S

Color and Shape: Neat

Molecular weight: 221.23

Ref: TR-H829675