Abstract
The thiazolidinedione moiety of ciglitazone and its analogues can be replaced by an alpha-alkoxy or alpha-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.
MeSH terms
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3T3 Cells
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Adipocytes / drug effects
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Animals
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Benzofurans / chemistry*
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Benzofurans / pharmacology
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Benzofurans / therapeutic use
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Carboxylic Acids / chemistry*
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Diabetes Mellitus, Type 2 / drug therapy
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Hypoglycemic Agents / chemistry*
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Hypoglycemic Agents / therapeutic use*
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Mice
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Mice, Mutant Strains
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Mice, Obese
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Molecular Structure
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Oxazoles / chemistry*
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Oxazoles / pharmacology
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Oxazoles / therapeutic use
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Stereoisomerism
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Structure-Activity Relationship
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Thiazoles / chemistry*
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Thiazolidinediones*
Substances
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Benzofurans
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Carboxylic Acids
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Hypoglycemic Agents
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Oxazoles
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Thiazoles
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Thiazolidinediones
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2-ethoxy-3-(2-((5-methyl-2-phenyloxazol-4-yl)methyl)benzofuran-5-yl)propionic acid
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3-(2-((5-methyl-2-phenyloxazol-4-yl)methyl)benzofuran-5-yl)-2-(propylsulfanyl)propionic acid
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ciglitazone