2-Haloaporphines as potent dopamine agonists.

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Ramsby S, Neumeyer JL, Grigoriadis D, Seeman P

2-Haloaporphines as potent dopamine agonists.

J Med Chem. 1989 Jun;32(6):1198-201.

PubMed ID

2524592 [ View in PubMed

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Abstract

The synthesis of 2-amino- and 2-halo-substituted aporphines is described. The key step is the substitution of a hydroxy group in the 2-position with an amino group effected by a Smiles rearrangement reaction of the 2-methylpropanamide derivative 6. The affinity of the new compounds for the dopamine D-2 receptor in the anterior pituitary gland was evaluated. 2-Fluoroapomorphine was the most potent compound, being 1.5 times more potent than (-)-apomorphine. The structure-activity relationships are discussed in relation to a previously proposed receptor model.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Apomorphine	Dopamine D2 receptor	Kd (nM)	127	N/A	N/A	Details
Apomorphine	Dopamine D2 receptor	Kd (nM)	0.66	N/A	N/A	Details