Synthesis and characterization of selective dopamine D2 receptor ligands using aripiprazole as the lead compound

Suwanna Vangveravong, Zhanbin Zhang, Michelle Taylor, Melissa Bearden, Jinbin Xu, Jinquan Cui, Wei Wang, Robert R. Luedtke, Robert H. MacH

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31 Scopus citations


A series of compounds structurally related to aripiprazole (1), an atypical antipsychotic and antidepressant used clinically for the treatment of schizophrenia, bipolar disorder, and depression, have been prepared and evaluated for affinity at D2-like dopamine receptors. These compounds also share structural elements with the classical D2-like dopamine receptor antagonists, haloperidol, N-methylspiperone, domperidone and benperidol. Two new compounds, 7-(4-(4-(2-methoxyphenyl)piperazin-1-yl)butoxy)- 3,4-dihydroquinolin-2(1H)-one oxalate (6) and 7-(4-(4-(2-(2-fluoroethoxy)phenyl) piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one oxalate (7) were found to (a) bind to the D2 receptor subtype with high affinity (Ki values <0.3 nM), (b) exhibit >50-fold D2 versus D3 receptor binding selectivity and (c) be partial agonists at both the D 2 and D3 receptor subtype.

Original languageEnglish
Pages (from-to)3502-3511
Number of pages10
JournalBioorganic and Medicinal Chemistry
Issue number11
StatePublished - 1 Jun 2011


  • Aripiprazole
  • Dopamine D receptor
  • Dopamine partial agonist


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