Synthesis and hypoglycemic activity of phenylalkyloxiranecarboxylic acid derivatives.
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.
D000818:Animals; D001786:Blood Glucose / Q000378:metabolism; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000633:toxicity; D055598:Chemical Phenomena; D002621:Chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000633:toxicity; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D005260:Female; D007004:Hypoglycemic Agents / Q000138:chemical synthesis* / Q000633:toxicity; D007928:Lethal Dose 50; D008297:Male; D009115:Muridae; D051381:Rats; D011919:Rats, Inbred Strains; D013329:Structure-Activity Relationship
D001786:Blood Glucose; D002264:Carboxylic Acids; D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D007004:Hypoglycemic Agents