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

C Haubmann; H Hübner; P Gmeiner

doi:10.1016/s0960-894x(99)00540-5

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.

Authors

C Haubmann¹, H Hübner, P Gmeiner

Affiliation

¹ Department of Medicinal Chemistry, Emil Fischer Center, Friedrich-Alexander University, Erlangen, Germany.

PMID: 10560741
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