Synthesis and structure-activity relationships of novel zwitterionic compounds as peroxisome proliferator activated receptor α/γ dual agonists with improved physicochemical properties

Chem Pharm Bull (Tokyo). 2013;61(12):1248-63. doi: 10.1248/cpb.c13-00513.

Abstract

We describe herein the design, syntheses and structure-activity relationships (SAR) of novel zwitterionic compounds as non-thiazolidinedion (TZD) based peroxisome proliferator activated receptor (PPAR) α/γ dual agonists. In the previous report, we obtained compound 1 showing potent PPARα/γ dual agonistic activities, together with a great glucose lowering effect in the db/db mice. However, this compound possessed fatal issues such as potent cytochrome P450 (CYP)3A4 direct inhibitory activity. Thus, we carried out the medicinal optimization to improve these while maintaining the potent PPAR agonistic activity. As a result, the issues were addressed by changing the furan ring to a low lipophilic 1,3,4-oxadiazole ring. Additionally, these oxadiazole derivatives exhibited a significant decrease in plasma glucose and plasma triglyceride levels without marked weight gain.

MeSH terms

  • Animals
  • Blood Glucose / analysis
  • Diabetes Mellitus, Type 2 / drug therapy
  • Drug Design
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / pharmacology
  • Mice
  • Oxadiazoles / chemistry*
  • Oxadiazoles / pharmacology*
  • PPAR alpha / agonists*
  • PPAR alpha / metabolism
  • PPAR gamma / agonists*
  • PPAR gamma / metabolism
  • Structure-Activity Relationship

Substances

  • Blood Glucose
  • Hypoglycemic Agents
  • Oxadiazoles
  • PPAR alpha
  • PPAR gamma
  • 1,3,4-oxadiazole