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J Med Chem. 2010 Mar 25;53(6):2646-50. doi: 10.1021/jm901291r.

Dopamine receptor ligands. Part 18: (1) modification of the structural skeleton of indolobenzazecine-type dopamine receptor antagonists.

Author information

1
Institut für Pharmazie, Lehrstuhl fur Pharmazeutische/Medizinische Chemie, Friedrich-Schiller-Universität Jena, Philosophenweg 14, D-07743 Jena, Germany.

Abstract

On the basis of the D(1/5)-selective dopamine antagonist LE 300 (1), an indolo[3,2-f]benzazecine derivative, we changed the annulation pattern of the heterocycles. The target compounds represent novel heterocyclic ring systems. The most constrained indolo[4,3a,3-ef]benzazecine 2 was inactive, but the indolo[4,3a,3-fg]benzazacycloundecene 3 showed antagonistic properties (functional Ca(2+) assay) with nanomolar affinities (radioligand binding) for all dopamine receptor subtypes, whereas the indolo[2,3-f]benzazecine 4 displayed a selectivity profile similar to 3 but with decreased affinities.

PMID:
20180564
DOI:
10.1021/jm901291r
[Indexed for MEDLINE]

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