cas 136401-70-2, 5-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione | Articles data ｜lookchem

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136401-70-2

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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.
Momose,Meguro,Ikeda,Hatanaka,Oi,Sohda
p. 1440 - 1445
(2007/10/02)

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Chemical Properties

Melting Point: 156-160 ºC
Density: 1.301±0.06 g/cm3(Predicted)
PKA: 7.59±0.20(Predicted)
PSA: 93.59000
LogP: 3.91820

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