Stereocontrolled Dopamine Receptor Binding and Subtype Selectivity of Clebopride Analogues Synthesized from Aspartic Acid

Gmeiner P, Einsiedel J, Hübner H (2003)


Publication Type: Journal article

Publication year: 2003

Journal

Publisher: Elsevier

Book Volume: 13

Pages Range: 3293-3296

Journal Issue: 19

DOI: 10.1016/S0960-894X(03)00678-4

Abstract

Employing the achiral 4-aminopiperidine derivative clebopride as a lead compound, chiral analogues were developed displaying dopamine receptor binding profiles that proved to be strongly dependent on the stereochemistry. Compared to the D1 receptor, the test compounds showed high selectivity for the D2-like subtypes including D2long, D2short, D3 and D4. The highest D4 and D3 affinities were observed for the cis-3-amino-4-methylpyrrolidines 3e and the enantiomer ent3e resulting in K i values of 0.23 and 1.8 nM, respectively. The benzamides of type 3 and 5 were synthesized in enantiopure form starting from (S)-aspartic acid and its unnatural optical antipode. © 2003 Elsevier Ltd. All rights reserved.

Authors with CRIS profile

How to cite

APA:

Gmeiner, P., Einsiedel, J., & Hübner, H. (2003). Stereocontrolled Dopamine Receptor Binding and Subtype Selectivity of Clebopride Analogues Synthesized from Aspartic Acid. Bioorganic & Medicinal Chemistry Letters, 13(19), 3293-3296. https://doi.org/10.1016/S0960-894X(03)00678-4

MLA:

Gmeiner, Peter, Jürgen Einsiedel, and Harald Hübner. "Stereocontrolled Dopamine Receptor Binding and Subtype Selectivity of Clebopride Analogues Synthesized from Aspartic Acid." Bioorganic & Medicinal Chemistry Letters 13.19 (2003): 3293-3296.

BibTeX: Download