Synthesis and dopamine receptor selectivity of the benzyltetrahydroisoquinoline, (R)-(+)-nor-roefractine.
(R)-(+)-nor-Roefractine (1) was synthesized by the Bischler-Napieralski route, using asymmetric reduction of the 1, 2-didehydro precursor imine with sodium (S)-N-CBZ-prolinyloxyborohydride. Compound 1 was able to displace [3H]-raclopride (a D2 dopamine receptor-selective ligand) from its specific binding sites in rat striatum with selectivity vs [3H]-SCH23390 (D1 dopamine receptor-selective ligand).
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Departamento de Farmacología, Farmacognosia y Farmacodinamia, Facultad de Farmacia, Universidad de Valencia, 46100 Burjassot, Valencia, Spain.
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D001552:Benzazepines / Q000494:pharmacology; D001667:Binding, Competitive / Q000187:drug effects; D018492:Dopamine Antagonists / Q000494:pharmacology; D007202:Indicators and Reagents; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000494:pharmacology; D008024:Ligands; D008968:Molecular Conformation; D017448:Receptors, Dopamine D2 / Q000187:drug effects*
D001552:Benzazepines; D018492:Dopamine Antagonists; D007202:Indicators and Reagents; D007546:Isoquinolines; D008024:Ligands; D017448:Receptors, Dopamine D2; C113213:nor-roefractine