Journal of Medicinal Chemistry 1982-12-01

Conformationally restricted congeners of dopamine derived from 2-aminoindan.

J G Cannon, J A Perez, R K Bhatnagar, J P Long, F M Sharabi

Index: J. Med. Chem. 25(12) , 1442-6, (1982)

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Abstract

Two series of N-substituted 2-aminoindan systems have been prepared: 4,5-dihydroxy-2-aminoindan (1) has a hydroxylation pattern analogous to the alpha conformer of dopamine, and 5,6-dihydroxy-2-aminoindan (2) has a hydroxylation pattern of the beta 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.