Asymmetric synthesis of chiral piperazinylpropylisoxazoline ligands for dopamine receptors

Ji Young Jung; Sun Ho Jung; Hun Yeong Koh

doi:10.1016/j.ejmech.2006.12.030

Asymmetric synthesis of chiral piperazinylpropylisoxazoline ligands for dopamine receptors

Eur J Med Chem. 2007 Jul;42(7):1044-8. doi: 10.1016/j.ejmech.2006.12.030. Epub 2007 Jan 13.

Authors

Ji Young Jung¹, Sun Ho Jung, Hun Yeong Koh

Affiliation

¹ Department of Chemistry and Institute of Basic Science, Sungshin Women's University, Seoul 136-742, South Korea.

PMID: 17316913
DOI: 10.1016/j.ejmech.2006.12.030

Abstract

The asymmetric synthesis of chiral piperazinylpropylisoxazoline analogues, (R)-(+)-1, 2 and (S)-(-)-1, 2 was accomplished through a seven-step sequence of reactions, which involved asymmetric 1,3-dipolar cycloaddition, alkyl chain extension, and reductive amination as key reactions. Chiral ligands (R)-(+)-1, 2 exhibited the higher binding affinity and selectivity for the D(3) receptor over the D(4) receptor than (S)-(-)-1, 2 ligands.

Publication types

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

MeSH terms

Dopamine Antagonists / chemical synthesis*
Dopamine Antagonists / metabolism
Dopamine Antagonists / pharmacology*
Isoxazoles / chemical synthesis*
Isoxazoles / metabolism
Isoxazoles / pharmacology*
Models, Molecular
Protein Binding
Receptors, Dopamine / chemistry
Receptors, Dopamine / metabolism*
Structure-Activity Relationship

Substances

Dopamine Antagonists
Isoxazoles
Receptors, Dopamine