PMID: 7381848May 1, 1980

Congeners of the alpha conformer of dopamine derived from octahydrobenz[h]isoquinoline

Journal of Medicinal Chemistry
J G CannonJ R Flynn


Two synthetic paths have been investigated for the preparation of cis and trans 8,9-dioxygenated octahydrobenz[h]isoquinoline ring systems. A sequence involving intramolecular Diels--Alder cyclization of a ring-opened intermediate product of a benzocyclobutene derivative was more satisfactory. The trans-fused isomers of the title compounds are frozen congeners of the alpha conformer of dopamine, isomeric with certain other tricyclic heterocycles which elicit a high degree of dopamine agonist activity. However, the present series of compounds exhibited a very low potency in an assay for dopamine-like actions. A possible reason for this inactivity has been suggested.


Apr 1, 1985·Medicinal Research Reviews·C Kaiser, T Jain

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