136401-59-7

Basic information

• Product Name: 5-{4-[2-(5-Methyl-pyridin-2-yl)-ethylsulfanyl]-benzyl}-thiazolidine-2,4-dione
• Synonyms: 5-{4-[2-(5-Methyl-pyridin-2-yl)-ethylsulfanyl]-benzyl}-thiazolidine-2,4-dione
• CAS NO: 136401-59-7
• Molecular Weight: 358.485
• Mol File: 136401-59-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-{4-[2-(5-Methyl-pyridin-2-yl)-ethylsulfanyl]-benzyl}-thiazolidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-{4-[2-(5-Methyl-pyridin-2-yl)-ethylsulfanyl]-benzyl}-thiazolidine-2,4-dione(136401-59-7)
• EPA Substance Registry System: 5-{4-[2-(5-Methyl-pyridin-2-yl)-ethylsulfanyl]-benzyl}-thiazolidine-2,4-dione(136401-59-7)

Safety Data

• Hazardous Substances Data: 136401-59-7(Hazardous Substances Data)

Upstream product

• 1193-02-8 4-aminotiophenol 
• 136401-90-6 4-[2-(5-Methyl-pyridin-2-yl)-ethylsulfanyl]-phenylamine 
• 3883-39-4 3-methyl-6-vinylpyridinium 
• 136401-80-4 2-Imino-5-{4-[2-(5-methyl-pyridin-2-yl)-ethylsulfanyl]-benzyl}-thiazolidin-4-one 

Relevant articles and documents

Studies on antidiabetic agents. X. Synthesis and biological activities of pioglitazone and related compounds

Various analogues of a new antidiabetic agent, pioglitazone (AD-4833, U-72107), were synthesized in order to study in more detail the structure-activity relationships of this class of drug. 5-(4-Pyridylalkylthiobenzyl)-2,4-thiazolidinediones (I), this-analogues of pioglitazone, were prepared via Meerwein arylation of the alkylthioanilines (IV). 5-(4-Pyridylalkoxybenzylidene)-2,4-thiazolidinediones (IIa) and related heterocyclic analogues (IIb) were synthesized by Knoevenagel condensation of the aldehydes (VIII) with the corresponding azolidinones. Compounds I and II were evaluated for hypoglycemic and hypolipidemic activity in genetically obese and diabetic yellow KK (KKA(y)) mice. Several 5-[4-[2-(2-pyridyl)ethoxy]-benzylidene]-2,4-thiazolidinediones (IIa) were equipotent to pioglitazone. However, the thia-analogues (I) and the benzylideneheterocycles (IIb) had decreased activity. Catalytic hydrogenation of the 5-benzylidene analogue (14) was found to be a convenient new synthetic method for pioglitazone. The configuration of 14 is also discussed.