New trisubstituted 1,2,4-triazole derivatives as potent ghrelin receptor antagonists. 3. Synthesis and pharmacological in vitro and in vivo evaluations

J Med Chem. 2008 Feb 14;51(3):689-93. doi: 10.1021/jm701292s. Epub 2008 Jan 15.

Abstract

Ghrelin receptor ligands based on trisubstituted 1,2,4-triazole structure were synthesized and evaluated for their in vitro binding and biological activity. In this study, we explored the replacement of the alpha-aminoisobutyryl moiety by aromatic or heteroaromatic groups. Compounds 5 and 34 acted as potent in vivo antagonists of hexarelin-stimulated food intake. These two compounds did not stimulate growth hormone secretion in rodents and did not antagonize growth hormone secretion induced by hexarelin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Obesity Agents / chemical synthesis*
  • Anti-Obesity Agents / chemistry
  • Anti-Obesity Agents / pharmacology
  • Eating / drug effects
  • Growth Hormone / metabolism
  • Humans
  • LLC-PK1 Cells
  • Oligopeptides / pharmacology
  • Picolines / chemical synthesis*
  • Picolines / chemistry
  • Picolines / pharmacology
  • Pyrazines / chemical synthesis*
  • Pyrazines / chemistry
  • Pyrazines / pharmacology
  • Radioligand Assay
  • Rats
  • Receptors, Ghrelin / antagonists & inhibitors*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Swine
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry
  • Triazoles / pharmacology

Substances

  • Anti-Obesity Agents
  • N-(1-(4-(2,4-dimethoxybenzyl)-5-phenethyl-4H-1,2,4-triazol-3-yl)-2-(1H-indol-3-yl)ethyl)picolinamide
  • N-(1-(5-(2-(1H-indol-3-yl)ethyl)-4-(2,4-dimethoxybenzyl)-4H-1,2,4-triazol-3-yl)-2-(1H-indol-3-yl)ethyl)pyrazine-2-carboxamide
  • Oligopeptides
  • Picolines
  • Pyrazines
  • Receptors, Ghrelin
  • Triazoles
  • hexarelin
  • Growth Hormone