Synthesis and characterization of selective dopamine D 2 receptor antagonists. 2. Azaindole, benzofuran, and benzothiophene analogs of L-741,626

Suwanna Vangveravong, Michelle Taylor, Jinbin Xu, Jinquan Cui, Wesley Calvin, Sonja Babic, Robert R. Luedtke, Robert H. MacH

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

A series of indole, 7-azaindole, benzofuran, and benzothiophene compounds have been prepared and evaluated for affinity at D 2-like dopamine receptors. These compounds share structural elements with the classical D 2-like dopamine receptor antagonists haloperidol, N-methylspiperone and benperidol. Two new compounds, 4-(4-iodophenyl)-1-((4-methoxy-1H-indol-3-yl) methyl)piperidin-4-ol (6) and 4-(4-iodophenyl)-1-((5-methoxy-1H-indol-3-yl) methyl)piperidin-4-ol (7), were found to have high affinity to and selectivity for D 2 versus D 3 receptors. Changing the aromatic ring system from an indole to other heteroaromatic ring systems reduced the D 2 binding affinity and the D 2 versus D 3 selectivity.

Original languageEnglish
Pages (from-to)5291-5300
Number of pages10
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number14
DOIs
StatePublished - 15 Jul 2010

Keywords

  • Benzofurans
  • Benzothiophenes
  • Dopamine D receptor
  • Indoles

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