1218776-98-7

Basic information

• Product Name: 5-[4-(benzyloxy)-3-methoxybenzylidene]-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[4-(benzyloxy)-3-methoxybenzylidene]-1,3-thiazolidine-2,4-dione
• CAS NO: 1218776-98-7
• Molecular Formula: C18H15NO4S
• Molecular Weight: 341.38
• Mol File: 1218776-98-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.345±0.06 g/cm3(Predicted)
• PKA: 7.39±0.20(Predicted)
• CAS DataBase Reference: 5-[4-(benzyloxy)-3-methoxybenzylidene]-1,3-thiazolidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[4-(benzyloxy)-3-methoxybenzylidene]-1,3-thiazolidine-2,4-dione(1218776-98-7)
• EPA Substance Registry System: 5-[4-(benzyloxy)-3-methoxybenzylidene]-1,3-thiazolidine-2,4-dione(1218776-98-7)

Safety Data

• Hazardous Substances Data: 1218776-98-7(Hazardous Substances Data)

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 100-44-7 benzyl chloride 
• 121-33-5 vanillin 

Downstream Products

• 1369567-95-2 3-benzyl-5-{(Z)-1-[4-(benzyloxy)-3-methoxyphenyl]methylidene}-1,3-thiazolane-2,4-dione 
• 364602-32-4 5-{(Z)-1-[4-(benzyloxy)-3-methoxyphenyl]methylidene}-3-(4-fluorobenzyl)-1,3-thiazolane-2,4-dione 

Relevant articles and documents

Microwave induced synthesis of the thiazolidine-2,4-dione motif and the efficient solvent free-solid phase parallel syntheses of 5-benzylidene- thiazolidine-2,4-dione and 5-benzylidene-2-thioxo-thiazolidine-4-one compounds

Novel microwave induced method for the synthesis of thiazolidine-2,4-dione motif under solvent phase conditions is developed. Further we report an efficient, microwave assisted method for the parallel syntheses of biologically important 5-benzylidene-thiazolidine-2,4-dione and 5-benzylidene-2- thioxothiazolidine-4-one compounds under solid-phase and solvent-free conditions. A comparative study between the developed microwave methods and the conventional methods is described. We have also illustrated the possible mechanism behind to address the reason why piperidine, acetic acid and silica gel enhanced the Knoevenagel condensation reaction.

Synthesis, biological activity and structure-activity relationships of new benzoic acid-based protein tyrosine phosphatase inhibitors endowed with insulinomimetic effects in mouse C2C12 skeletal muscle cells

Insulin resistance is a complex altered metabolic condition characterized by impaired insulin signaling and implicated in the pathogenesis of serious human diseases, such as diabetes, obesity, neurodegenerative pathologies. In pursuing our aim to identify new agents able to improve cellular insulin sensitivity, we have synthesized new 4-[(5-arylidene-4-oxo-2-phenylimino/ oxothiazolidin-3-yl)methyl]benzoic acids (5, 8) and evaluated their inhibitory activity towards human protein tyrosine phosphatases PTP1B, LMW-PTP and TCPTP, enzymes which are involved in the development of insulin resistance. Compounds 5 and 8 showed from moderate to significant selectivity toward PTP1B over both the highly homologous TCPTP and the two isoforms of human LMW-PTP. In addition, most of the tested compounds selectively inhibited LMW-PTP IF1 over the isoform IF2. Docking studies into the active sites of PTP1B and LMW-PTP aided the rationalization of the observed PTP inhibitory profile. Moreover, most tested compounds were capable to induce the insulin metabolic pathway in mouse C2C12 skeletal muscle cells by remarkably stimulating both IRβ phosphorylation and 2-deoxyglucose cellular uptake.