Synthesis and structure-activity relationships of (R)-1-alkyl-3-[2-(2-amino)phenethyl]-5-(2-fluorophenyl)-6-methyluracils as human GnRH receptor antagonists

Bioorg Med Chem Lett. 2004 May 3;14(9):2269-74. doi: 10.1016/j.bmcl.2004.02.004.

Abstract

The synthesis of a series of (R)-1-alkyl-3-[2-(2-amino)phenethyl]-5-(2-fluorophenyl)-6-methyluracils is discussed. SAR around N-1 of the uracil was explored, which led to the discovery that an electron-deficient 2,6-disubstituted benzyl group is required for optimal receptor binding. The best compound from the series had binding affinity of 0.7 nM (K(i) for the human GnRH receptor, which was 8-fold better than the 2,6-difluorobenzyl analog.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Humans
  • Receptors, LHRH / antagonists & inhibitors*
  • Structure-Activity Relationship
  • Uracil / analogs & derivatives*
  • Uracil / chemical synthesis
  • Uracil / chemistry*
  • Uracil / pharmacology

Substances

  • Receptors, LHRH
  • Uracil
  • 6-methyluracil