Synthesis and dopaminergic properties of some exo- and endo-2-aminobenzonorbornenes designed as rigid analogs of dopamine

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Abstract
Stereospeciic syntheses of exo-2-amino-5,6-dihydroxybenzonorbornene (11f), exo-2-amino-6,7-dihydroxybenzonorbornene (11b), exo-2-amino-7,8-dihydroxybenzonorbornene (11g) and endo-2-amino-6,7-dihydroxybenzonorbornene (14d), rigid analogs of dopamine, are described. 11h and 14d, their N-methyl and N,N-dimethyl derivatives, and 11f and 11g were inactive as dopamine agonists when evaluated for dopaminergic activity by their ability to induce stereotyped behaivor in mice after s.c. injection and by their ability to cause hyperactivity in rats after bilateral injection into the nucleus accumbens. 11f, 11g, 11h and the N-methyl derivatives were all effective in displacing [3H]-2-amino-6,7-dihydroxytetralin ([3H]ADTN) and [3H]-N-n-propylnorapomorphine ([3H]NPA) from rat striatal membranes.
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