Asymmetric synthesis of chiral piperazinylpropylisoxazoline ligands for dopamine receptors.

Eur J Med Chem

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

Published: July 2007

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.

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http://dx.doi.org/10.1016/j.ejmech.2006.12.030DOI Listing

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