The discovery of novel small molecule non-peptide gonadotropin releasing hormone (GnRH) receptor antagonists

Bioorg Med Chem Lett. 2002 Dec 2;12(23):3467-70. doi: 10.1016/s0960-894x(02)00755-2.

Abstract

A novel series of non-peptide derivatives 1, 14, and 15 that bind with high affinity to the human GnRH receptors is discussed. The discovery was made from screening our in-house libraries that contained the active structure 2 along with a trace amount of a second active structure 1 that was derived from an acid-induced rearrangement. From this structure type 1, a series of guanidine and non-guanidine containing analogues were prepared and tested as GnRH receptor antagonists. Compounds derived from this series bind to both human and rat GnRH receptors and antagonize GnRH-mediated increases in inositol phosphate production in cells containing recombinant human receptors. These compounds or their analogues may be useful as therapeutic agents for the treatment of hormone-dependent pathologies including prostate, breast and ovarian cancers.

MeSH terms

  • Animals
  • Drug Design
  • Guanidine / analogs & derivatives*
  • Guanidine / pharmacology
  • Hormone Antagonists / chemistry
  • Hormone Antagonists / pharmacology
  • Humans
  • Phosphoric Monoester Hydrolases / biosynthesis
  • Protein Binding
  • Rats
  • Receptors, LHRH / antagonists & inhibitors*
  • Receptors, LHRH / metabolism
  • Recombinant Proteins / antagonists & inhibitors
  • Recombinant Proteins / metabolism
  • Structure-Activity Relationship

Substances

  • Hormone Antagonists
  • Receptors, LHRH
  • Recombinant Proteins
  • Phosphoric Monoester Hydrolases
  • myo-inositol-1 (or 4)-monophosphatase
  • Guanidine