Synthesis and SAR of benzyl and phenoxymethylene oxadiazole benzenesulfonamides as selective beta3 adrenergic receptor agonist antiobesity agents

Bioorg Med Chem Lett. 2000 Jul 3;10(13):1431-4. doi: 10.1016/s0960-894x(00)00268-7.

Abstract

Benzyl and phenoxymethylene substituted oxadiazoles are potent and orally bioavailable beta3 adrenergic receptor (AR) agonists. The 4-trifluormethoxy substituted 5-benzyl oxadiazole 5f has an EC50 of 8 nM in the beta3 AR agonist assay with 100-fold selectivity over beta1 and beta2 AR binding inhibition activity. Its oral bioavailability in dogs is 30 +/- 4%, with a half-life of 3.8 +/- 0.4 h. In the anesthetized rhesus, 5f evoked a dose-dependent glycerolemia (ED50Gly = 0.15 mg/kg). Under these conditions a heart rate increase of 15% was observed at a dose level of 10 mg/kg.

MeSH terms

  • Adrenergic beta-3 Receptor Agonists*
  • Adrenergic beta-Agonists / chemical synthesis
  • Adrenergic beta-Agonists / chemistry
  • Adrenergic beta-Agonists / pharmacology*
  • Animals
  • Anti-Obesity Agents / chemical synthesis
  • Anti-Obesity Agents / chemistry
  • Anti-Obesity Agents / pharmacology*
  • Biological Availability
  • CHO Cells
  • Cricetinae
  • Dogs
  • Drug Design
  • Glycerol / metabolism
  • Heart Rate / drug effects
  • Humans
  • Macaca mulatta
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / chemistry
  • Oxadiazoles / pharmacology*
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology*

Substances

  • Adrenergic beta-3 Receptor Agonists
  • Adrenergic beta-Agonists
  • Anti-Obesity Agents
  • Oxadiazoles
  • Sulfonamides
  • Glycerol