Stereochemical studies of adrenergic drugs. Diastereomeric 2-amino-1-phenylcyclobutanols

Journal of Medicinal Chemistry
1976.0

Abstract

The synthesis of the cis- and trans-2-amino-1-phenylcyclobutanols 2 and 3 is described. The results of the potentiation of the action of (-)-norepinephrine by these two compounds are discussed. Three 3,7-diazabicyclo[3.3.l]nonane derivatives (4) with a structural similarity to the analgetic agent azabicyclane (1) were prepared. The amino alcohol 4a was found to prefer a conformation wherein the six-membered ring to which the hydroxyl group is syn is in the boat form. These three compounds had increased basicity in comparison with 1 due to various forces stabilizing their monocationic states. Compounds 4a-c did not show analgetic activity at the dose levels tested.

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