85259-44-5

Basic information

• Product Name: 4-<2-(6-methyl-2-pyridyl)ethoxy>benzaldehyde
• Synonyms: 4-<2-(6-methyl-2-pyridyl)ethoxy>benzaldehyde
• CAS NO: 85259-44-5
• Molecular Weight: 241.29
• Mol File: 85259-44-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-<2-(6-methyl-2-pyridyl)ethoxy>benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-<2-(6-methyl-2-pyridyl)ethoxy>benzaldehyde(85259-44-5)
• EPA Substance Registry System: 4-<2-(6-methyl-2-pyridyl)ethoxy>benzaldehyde(85259-44-5)

Safety Data

• Hazardous Substances Data: 85259-44-5(Hazardous Substances Data)

Upstream product

• 1194-02-1 4-fluorobenzonitrile 
• 934-78-1 2-(6-methylpyridin-2-yl)-ethanol 
• 85003-45-8 methyl 2-chloro-3-<4-<2-(6-methyl-2-pyridyl)ethoxy>phenyl>propionate 
• 85259-42-3 4-<2-(6-methyl-2-pyridyl)ethoxy>cinnamic acid 
• 136401-95-1 4-<2-(6-methyl-2-pyridyl)ethoxy>benzonitrile 

Downstream Products

• 85258-89-5 5-{4-[2-(6-Methyl-pyridin-2-yl)-ethoxy]-phenyl}-thiazolidine-2,4-dione 
• 136401-66-6 5-<4-<2-(6-Methyl-2-pyridyl)ethoxy>benzylidene>-2,4-thiazolidinedione 
• 136401-73-5 5-<4-<2-(6-Methyl-2-pyridyl)ethoxy>benzylidene>rhodanine-3-acetic Acid 
• 136401-72-4 5-<4-<2-(6-Methyl-2-pyridyl)ethoxy>benzylidene>rhodanine 
• 136401-75-7 5-<4-<2-(6-Methyl-2-pyridyl)ethoxy>benzylidene>-2-thiohydantoin 
• 136401-74-6 5-<4-<2-(6-Methyl-2-pyridyl)ethoxy>benzylidene>hydantoin 
• 136401-76-8 5-<4-<2-(6-Methyl-2-pyridyl)ethoxy>benzylidene>-2-thioxo-5-thiazolidinone 

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.

Method for producing thiazolidinedione derivatives

A compound of the formula: STR1 (wherein R1 is hydrogen or a lower alkyl) can be produced advantageously by (1) reacting a compound of the formula: STR2 (wherein R1 has a meaning given above) with a halogenating agent or sulfonyl halide to give a compound of the formula: STR3 (wherein R1 has a meaning given above and X is a halogen or an alkyl- or aryl-sulfonyloxy), (2) reacting the resulting compound with a compound of the formula: STR4 to give a compound of the formula: (wherein R1 has the meaning given above), (3) reacting the resulting compound with a compound of the formula: STR5 to give a compound of the formula: STR6 (wherein R1 has the meaning given above), and (4) subjecting the resulting compound to catalytic reduction.