Resolution and absolute configuration of the potent dopamine agonist N,N-diethyl-N'-[(3 alpha, 4a alpha, 10a beta)-1,2,3,4,4a,5,10,10a- -octahydro-6-hydroxy-1-propyl-3-benzo[g]quinolinyl]sulfamide

J Med Chem. 1985 Oct;28(10):1540-2. doi: 10.1021/jm00148a030.

Abstract

The synthesis and preliminary pharmacological evaluation of the optical antipodes of the title compound (+/-)-1 (CV 205-502) is presented. The dopaminomimetic activity is shown to reside entirely in the (-) enantiomer. Crystallographic analysis has proven that the absolute configuration of the active (-) enantiomer corresponds to that of its ergoline analogue 3 (CQ 32-084) and of apomorphine (5).

MeSH terms

  • Aminoquinolines* / pharmacology
  • Animals
  • Apomorphine / pharmacology
  • Crystallography
  • Male
  • Molecular Conformation
  • Rats
  • Receptors, Dopamine / drug effects*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Aminoquinolines
  • Receptors, Dopamine
  • quinagolide
  • Apomorphine