Selection, synthesis, and structure-activity relationship of tetrahydropyrido[4,3-d]pyrimidine-2,4-diones as human GnRH receptor antagonists

Bioorg Med Chem. 2007 Aug 15;15(16):5590-603. doi: 10.1016/j.bmc.2007.05.029. Epub 2007 May 17.

Abstract

The present article describes a selection of a new class of small molecule antagonists for the h-GnRH receptor, their preparation, and evaluation in vitro. Three computational methods were combined into a consensus score, to rank order virtual templates. The top 5% of templates were further evaluated in silico and assessed for novelty and synthetic accessibility. The tetrahydropyrido[4,3-d]pyrimidine-2,4-dione core was selected for synthesis and evaluated in vitro. Using an array approach for analog design and synthesis, we were able to drive the binding below 10nM for the h-GnRH receptor after two rounds of optimization.

MeSH terms

  • Databases, Factual
  • Ethylamines / chemistry
  • Humans
  • Hydrogen / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry*
  • Pyrimidines / pharmacology*
  • Receptors, LHRH / antagonists & inhibitors*
  • Receptors, LHRH / metabolism
  • Structure-Activity Relationship

Substances

  • Ethylamines
  • Pyrimidines
  • Receptors, LHRH
  • Hydrogen
  • pyrimidine
  • ethylamine