Abstract
cis- and trans-2,3,3a,4,5,9b-Hexahydro-1 H-benz[ e]indoles were synthesized as conformationally rigid analogues of 3-phenylpyrrolidine and evaluated for dopamine (DA) D 2S and D 3 receptor binding affinity. The tricyclic benz[ e]indole nucleus was constructed by a previously reported reductive amination-cyclization procedure. Several unexpected side products were isolated and characterized using the general method. The trans-diastereoisomers exhibited greater affinities for the DA D 3 receptor than the corresponding cis-isomers. In both the cis- and trans- series the greatest affinity for DA D 3 receptors was shown by compounds substituted with N- n-propyl or N-allyl groups. The cis-(±)- N-allyl derivative 21e demonstrated a D 2S/D 3 selectivity of 290. Resolution of cis-(±)- 5 and trans-(±)- 21c into individual enantiomers showed that in both series the more active isomer had 3a R absolute configuration. These novel ligands may be useful tools for gaining additional information about the DA D 3 receptor.
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