Synthesis and structure-activity relationships of thieno[2,3-b]pyrroles as antagonists of the GnRH receptor

Bioorg Med Chem Lett. 2007 Dec 1;17(23):6448-54. doi: 10.1016/j.bmcl.2007.09.099. Epub 2007 Oct 4.

Abstract

A new class of small-molecule GnRH antagonists, the thieno[2,3-b]pyrroles, was designed. Herein, the synthesis and structure-activity relationships are described. Substitution at the C4 position was investigated; during this study, it was observed that introducing piperazines and piperidines improved the physical properties of the compounds while retaining good in vitro potency. This exploration led to the discovery of amidopiperidines with improved pharmacokinetic properties.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Humans
  • Pyrroles / chemical synthesis*
  • Pyrroles / pharmacology
  • Rats
  • Receptors, LHRH / antagonists & inhibitors*
  • Receptors, LHRH / metabolism
  • Receptors, LHRH / physiology
  • Structure-Activity Relationship
  • Thiophenes / chemical synthesis*
  • Thiophenes / pharmacology

Substances

  • Pyrroles
  • Receptors, LHRH
  • Thiophenes