Piperidinylpyrroles: design, synthesis and binding properties of novel and selective dopamine D4 receptor ligands

Bioorg Med Chem Lett. 1999 Nov 1;9(21):3143-6. doi: 10.1016/s0960-894x(99)00540-5.

Abstract

Piperidinylpyrroles of type 3 were synthesized through a modified Paal-Knorr reaction. For the introduction of pyrrole-substituents high yielding transformations including Sonogashira cross-coupling reactions were utilized. Employment of the reagent TosMIC gave access to the regioisomeric oxazolyl derivatives 7 and 11 which showed the highest dopamine D4 receptor binding of the series investigated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Binding, Competitive
  • Cattle
  • Dopamine Antagonists / chemical synthesis*
  • Dopamine Antagonists / pharmacology
  • Drug Design
  • Humans
  • Ligands
  • Molecular Structure
  • Protein Binding
  • Pyrroles / chemical synthesis*
  • Pyrroles / pharmacology
  • Receptors, Dopamine D2 / metabolism*
  • Receptors, Dopamine D4
  • Spiperone / metabolism

Substances

  • DRD4 protein, human
  • Dopamine Antagonists
  • Ligands
  • Pyrroles
  • Receptors, Dopamine D2
  • Receptors, Dopamine D4
  • Spiperone