Asymmetric synthesis of chiral piperazinylpropylisoxazoline ligands for dopamine receptors.

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Jung JY, Jung SH, Koh HY

Asymmetric synthesis of chiral piperazinylpropylisoxazoline ligands for dopamine receptors.

Eur J Med Chem. 2007 Jul;42(7):1044-8. Epub 2007 Jan 13.

PubMed ID

17316913 [ View in PubMed

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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.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Haloperidol	Dopamine D2 receptor	Ki (nM)	3.3	N/A	N/A	Details
Haloperidol	Dopamine D3 receptor	Ki (nM)	6.4	N/A	N/A	Details