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.
- 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