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Synthesis and Dopamine Receptor Binding of 3‐Phenylazepino[5,4,3‐c,d]indole Derivatives

The 3‐phenylazepino[5,4,3‐c,d]indole derivatives 5 and 9–11, representing heterocyclic analogs of the selective dopamine D‐1 receptor ligands of the 3‐phenylbenzazepine class, were synthesized starting from the indole‐4‐carboxylate 7. Receptor binding studies employing bovine striatal membranes demonstrated that the test compounds 5, 10, and 11 are able to displace the D‐1 selective radioligand [3H]‐SCH 23390 as well as the D‐2 antagonist [3H]‐spiperone. Compound 5b turned out to be the most potent and selective ligand (ki = 1.8 μM for D‐1 and ki = 8.9 μM for D‐2). It is assumed that the moderate selectivity of 5b is due to the conformational inequality of the 7‐membered rings when compared to the benzazepines. This results in a spatial arrangement of the phenyl substituent which is not able to interact with a ‘subtype selectivity‐inducing site’.