Synthesis and D2-like binding affinity of 4,5-dihydro-1H-benzo[g]indole-3-carboxamide derivatives as conformationally restricted 5-phenyl-pyrrole-3-carboxamide analogs

Gérard A. Pinna, Maria M. Curzu, Mario Sechi, Giorgio Chelucci, Paola Vianello, Elisabetta Maciocco

Research output: Contribution to journalArticle

Abstract

A series of 4,5-dihydro-1H-benzo[g]-indole-3-carboxamide derivatives 2a-g were synthesized as conformationally restricted analogs of the dopamine D2-like 5-phenylpyrrole-3-carboxamide ligands and evaluated for their affinity for the dopamine D2-like receptors. In this series, N3-[(1-ethyltetrahydro-1H-2-pyrrolyl)methyl]-4,5-dihydro-1H-benzo[g]indole-3 -carboxamide (2a) showed the highest affinity for D2-like receptors (IC50 = 160 nM). Replacement of the N-(1-ethyl-2-pyrrolidinyl)methyl side chain with a 2-(N,N-diethylamino)ethyl or a 1-benzyl-4-piperidinyl group (2b, 2d) decreased affinity for the D2-like receptor. The other compounds tested were found to be devoid of D2-like binding affinity.

Original languageEnglish
Pages (from-to)684-689
Number of pages6
JournalFarmaco
Volume53
Issue number10-11
DOIs
Publication statusPublished - Nov 1998

Keywords

  • 4,5-Dihydro-1H-benzo[g]indole-3-carboxamide derivatives
  • D-like receptor binding affinity
  • Structure-activity relationships

ASJC Scopus subject areas

  • Drug Discovery
  • Pharmaceutical Science

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