Conformationally Restricted Congeners of Dopamine Derived from 2-Aminoindan

Article abstract of DOI:10.1021/jm00354a010

Two series of N-substituted 2-aminoindan systems have been prepared: 4,5-dihydroxy-2-aminoindan (1) has a hydroxylation pattern analogous to the α-conformer of dopamine, and 5,6-dihydroxy-2-aminoindan (2) has a hydroxylation pattern of the β conformer of dopamine.All members of both series demonstrated only extremely weak binding to calf caudate homogenate.Certain N-alkylated 4,5-dihydroxyindans were violent emetics in the dog and were potent in blockade of the effect of stimulation of the cardioaccelerator nerve of the cat.In contrast, the 5,6-dihydroxy series displayed low or no activity/potency in these assays.Conformational analysis of the 2-aminoindan system is described and discussed.