Synthesis and hypoglycemic activity of phenylalkyloxiranecarboxylic acid derivatives

J Med Chem. 1982 Feb;25(2):109-13. doi: 10.1021/jm00344a003.

Abstract

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.

MeSH terms

  • 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

Substances

  • Blood Glucose
  • Carboxylic Acids
  • Epoxy Compounds
  • Ethers, Cyclic
  • Hypoglycemic Agents