Enantio- and diastereocontrolled dopamine D1, D2, D3 and D4 receptor binding of N-(3-pyrrolidinylmethyl)benzamides synthesized from aspartic acid

C Thomas; H Hübner; P Gmeiner

doi:10.1016/s0960-894x(99)00086-4

Enantio- and diastereocontrolled dopamine D1, D2, D3 and D4 receptor binding of N-(3-pyrrolidinylmethyl)benzamides synthesized from aspartic acid

Bioorg Med Chem Lett. 1999 Mar 22;9(6):841-6. doi: 10.1016/s0960-894x(99)00086-4.

Authors

C Thomas¹, H Hübner, P Gmeiner

Affiliation

¹ Institut für Pharmazie und Lebensmittelchemie, Universität Erlangen-Nürnberg, Erlangen, Germany.

PMID: 10206547
DOI: 10.1016/s0960-894x(99)00086-4

Abstract

Subreceptor selectivity tuning of N-(3-pyrrolidinyl)benzamides leading to the selective dopamine D3 ligand ent1h and the derivatives 1g and 1e/ent1e which preferably recognize human D2 or D4 receptors, respectively, is described. Binding profiles were controlled by both, absolute and relative configuration. The enantiopure target compounds were synthesized from aspartic acid.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Aspartic Acid / analogs & derivatives*
Benzamides / chemical synthesis
Benzamides / pharmacology*
Cattle
Humans
Kinetics
Models, Chemical
Pyrrolidines / chemical synthesis
Pyrrolidines / pharmacology*
Receptors, Dopamine / metabolism*

Substances

Benzamides
Pyrrolidines
Receptors, Dopamine
Aspartic Acid