136401-70-2

Basic information

• Product Name: 5-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione
• Synonyms: 5-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione
• CAS NO: 136401-70-2
• Molecular Formula: C₁₉H₁₈N₂O₃S
• Molecular Weight: 354.42
• Mol File: 136401-70-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 156-160 ºC
• Appearance: /
• Density: 1.301±0.06 g/cm3(Predicted)
• Refractive Index: 1.653
• PKA: 7.59±0.20(Predicted)
• CAS DataBase Reference: 5-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione(136401-70-2)
• EPA Substance Registry System: 5-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione(136401-70-2)

Safety Data

• Hazardous Substances Data: 136401-70-2(Hazardous Substances Data)

Usage

General Description

5-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione is a complex synthetic chemical compound. The chemistry of this compound is characterized by various functional groups such as Ethylpyridinyl, Ethoxy, Benzylidene, and Thiazolidinedione. It belongs to the organic class of compounds known as benzylideneanilines, which are characterized by an aniline group substituted at the benzene ring by a benzylidene moiety. Thiazolidinedione, another major functional group present, correlates with its potential biological activity. However, detailed information regarding its physical characteristics, chemical stability, potential uses, or biological activity is not readily available, indicating that this could be a novel compound under investigation.

InChI:InChI=1/C19H18N2O3S/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17/h3-8,11-12H,2,9-10H2,1H3,(H,21,22,23)

Upstream product

• 136402-00-1 4-[2-(5-ethylpyridin-2-yl)ethoxy] benzonitrile 
• 114393-97-4 4-[2-(5-ethylpyridyl)ethoxy]benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 1194-02-1 4-fluorobenzonitrile 
• 5223-06-3 5-ethyl-2-(2-hydroxyethyl)pyridine 
• 136401-69-9 5-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]benzylidene}-2,4-thiazolidinedione 

Downstream Products

• 105355-27-9 Pioglitazone 
• 1207681-45-5 (5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione hydrochloride 
• 1263978-86-4 (5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione tosylate 
• 1263978-84-2 (5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione L-tartrate 
• 959687-65-1 (R)-5-({p-[2-(5-ethyl-2-pyridyl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione 
• 959687-66-2 (S)-5-({p-[2-(5-ethyl-2-pyridyl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione 

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.