Congeners of the alpha conformer of dopamine derived from octahydrobenz[h]isoquinoline.
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.
D000818:Animals; D002415:Cats; D055598:Chemical Phenomena; D002621:Chemistry; D004298:Dopamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D006339:Heart Rate / Q000187:drug effects; D007546:Isoquinolines; D008968:Molecular Conformation; D009474:Neurons / Q000187:drug effects
D007546:Isoquinolines; D004298:Dopamine