Synthesis and hypoglycemic activity of phenylalkyloxiranecarboxylic acid derivatives

• Published in: Journal of medicinal chemistry Vol. 25; no. 2; pp. 109 - 113
• Main Authors: Eistetter, Klaus, Wolf, Horst P. O
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 01-02-1982
• Subjects: Animals; Blood Glucose - metabolism; Carboxylic Acids - chemical synthesis; Carboxylic Acids - toxicity; Chemical Phenomena; Chemistry; Epoxy Compounds - chemical synthesis; Epoxy Compounds - toxicity; Ethers, Cyclic - chemical synthesis; Female; Hypoglycemic Agents - chemical synthesis; Hypoglycemic Agents - toxicity; Lethal Dose 50; Male; Muridae; Rats; Rats, Inbred Strains; Structure-Activity Relationship
• ISSN: 0022-2623; 1520-4804
• DOI: 10.1021/jm00344a003

A series of new 2-(phenylalkyl)oxirane-2-carboxylic acids has been synthesized and studied for its effects on the concentration of blood glucose. Most of the compounds exhibit remarkable blood glucose lowering activities in fasted rats. Structure-activity studies reveal that substituents like Cl or CF3 on the phenyl ring and a chain length of three to five carbon atoms lead to the most effective substances. Among these compounds, ethyl 2-[5-(4-chlorophenyl)pentyl]oxirane-2-carboxylate (36) exhibits the most favorable activity.