Benzimidazoles as non-peptide luteinizing hormone-releasing hormone (LHRH) antagonists. Part 3: Discovery of 1-(1H-benzimidazol-5-yl)-3-tert-butylurea derivatives

Bioorg Med Chem Lett. 2005 May 2;15(9):2265-9. doi: 10.1016/j.bmcl.2005.03.030.

Abstract

1-(1H-Benzimidazol-5-yl)-3-tert-butylurea derivatives have been identified as a novel class of non-peptide luteinizing hormone-releasing hormone (LHRH) antagonists. Herein, we disclose the synthesis and structure-activity relationships (SAR) of this class resulting in the identification of compound 12c, with dual functional activity on human and rat receptors (rat LHRH: IC50=120 nM; human LHRH: IC50=18 nM). These SAR studies suggest that 1-(1H-benzimidazol-5-yl)-3-tert-butylurea is a new pharmacophore for small molecule LHRH antagonists.

MeSH terms

  • Animals
  • Benzimidazoles / chemical synthesis
  • Benzimidazoles / pharmacology*
  • Gonadotropin-Releasing Hormone / antagonists & inhibitors*
  • Humans
  • Kinetics
  • Models, Molecular
  • Molecular Structure
  • Rats
  • Structure-Activity Relationship
  • Urea / analogs & derivatives*
  • Urea / chemical synthesis
  • Urea / pharmacology

Substances

  • Benzimidazoles
  • Gonadotropin-Releasing Hormone
  • Urea