Hypoglycemic Activity of a Series of α-Alkylthio and α-Alkoxy Carboxylic Acids Related to Ciglitazone

The thiazolidinedione moiety of ciglitazone and its analogues can be replaced by an α-alkoxy or α-thioether carboxylic acid group. The influence of the nature of the R group, the length of the connector to the aromatic backbone of the molecule, and the stereochemistry have been studied. The most pot...

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Veröffentlicht in:	Journal of medicinal chemistry 1996-09, Vol.39 (20), p.3897-3907
Hauptverfasser:	Hulin, Bernard, Newton, Linda S, Lewis, Diana M, Genereux, Paul E, Gibbs, E. Michael, Clark, David A
Format:	Artikel
Sprache:	eng
Schlagworte:	3T3 Cells Adipocytes - drug effects Animals Benzofurans - chemistry Benzofurans - pharmacology Benzofurans - therapeutic use Biological and medical sciences Carboxylic Acids - chemistry Diabetes Mellitus, Type 2 - drug therapy General and cellular metabolism. Vitamins Hypoglycemic Agents - chemistry Hypoglycemic Agents - therapeutic use Medical sciences Mice Mice, Mutant Strains Mice, Obese Molecular Structure Oxazoles - chemistry Oxazoles - pharmacology Oxazoles - therapeutic use Pharmacology. Drug treatments Stereoisomerism Structure-Activity Relationship Thiazoles - chemistry Thiazolidinediones
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Zusammenfassung:	The thiazolidinedione moiety of ciglitazone and its analogues can be replaced by an α-alkoxy or α-thioether carboxylic acid group. The influence of the nature of the R group, the length of the connector to the aromatic backbone of the molecule, and the stereochemistry have been studied. The most potent compounds have glucose-lowering activity at doses as low as 0.01 mg/kg.
ISSN:	0022-2623 1520-4804
DOI:	10.1021/jm960230h