Discovery and pharmacological evaluation of growth hormone secretagogue receptor antagonists

J Med Chem. 2006 Jul 27;49(15):4459-69. doi: 10.1021/jm060461g.

Abstract

The discovery and pharmacological evaluation of potent, selective, and orally bioavailable growth hormone secretagogue receptor (GHS-R) antagonists are reported. Previously, 2,4-diaminopyrimidine-based GHS-R antagonists reported from our laboratories have been shown to be dihydrofolate reductase (DHFR) inhibitors. By comparing the X-ray crystal structure of DHFR docked with our GHS-R antagonists and GHS-R modeling, we designed and synthesized a series of potent and DHFR selective GHS-R antagonists with good pharmacokinetic (PK) profiles. An amide derivative 13d (Ca2+ flux IC50 = 188 nM, [brain]/[plasma] = 0.97 @ 8 h in rat) showed a 10% decrease in 24 h food intake in rats, and over 5% body weight reduction after 14-day oral treatment in diet-induced obese (DIO) mice. In comparison, a urea derivative 14c (Ca2+ flux IC50 = 7 nM, [brain]/[plasma] = 0.0 in DIO) failed to show significant effect on food intake in the acute feeding DIO model. These observations demonstrated for the first time that peripheral GHS-R blockage with small molecule GHS-R antagonists might not be sufficient for suppressing appetite and inducing body weight reduction.

MeSH terms

  • Administration, Oral
  • Amides / chemical synthesis
  • Amides / pharmacology
  • Aminopyridines / chemical synthesis*
  • Aminopyridines / pharmacology
  • Animals
  • Anti-Obesity Agents / chemical synthesis*
  • Anti-Obesity Agents / pharmacology
  • Appetite Depressants / chemical synthesis
  • Appetite Depressants / pharmacology
  • Biological Availability
  • Body Weight / drug effects
  • Cell Line
  • Crystallography, X-Ray
  • Eating / drug effects
  • Humans
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Mice, Obese
  • Models, Molecular
  • Molecular Structure
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, G-Protein-Coupled / antagonists & inhibitors*
  • Receptors, Ghrelin
  • Structure-Activity Relationship
  • Urea / analogs & derivatives
  • Urea / chemical synthesis
  • Urea / pharmacology

Substances

  • Amides
  • Aminopyridines
  • Anti-Obesity Agents
  • Appetite Depressants
  • Receptors, G-Protein-Coupled
  • Receptors, Ghrelin
  • Urea