Dopamine/serotonin receptor ligands. 9. Oxygen-containing midsized heterocyclic ring systems and nonrigidized analogues. A step toward dopamine D5 receptor selectivity.

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Wittig TW, Decker M, Lehmann J

Dopamine/serotonin receptor ligands. 9. Oxygen-containing midsized heterocyclic ring systems and nonrigidized analogues. A step toward dopamine D5 receptor selectivity.

J Med Chem. 2004 Aug 12;47(17):4155-8.

PubMed ID

15293986 [ View in PubMed

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Abstract

Eleven-membered heterocycles (dibenz[g,j]-1-oxa-4-azacycloundecenes) and open-chain analogues were synthesized and investigated for affinities to human dopamine receptor subtypes. The moderately rigidized rings displayed nanomolar and subnanomolar Ki values at D1-like receptors with a significant D1 to D2 and a slight D5 to D1 selectivity. The open-chain analogues showed lower affinities but significant D1 to D2 selectivities. Compound 3 (Ki(D5) = 0.57 nmol) showed antagonistic or inverse agonistic binding characteristics in a functional Ca assay.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Haloperidol	Dopamine D1 receptor	Ki (nM)	82	N/A	N/A	Details
Haloperidol	Dopamine D2 receptor	Ki (nM)	2.2	N/A	N/A	Details
Haloperidol	Dopamine D3 receptor	Ki (nM)	7.8	N/A	N/A	Details