Synthesis and binding to β-adrenergic receptors of p-aminobenzyl analogues of practolol and atenolol

Article abstract of DOI:10.1002/jps.2600810422

The p-aminobenzyl analogues (8a and 8b, respectively) of the cardioselective β-adrenergic receptor antagonists practolol and atenolol were prepared from the corresponding phenoxymethyloxiranes in 30 and 13% yields, respectively. The dissociation constants for the β-adrenergic receptor were measured in membrane preparations of rat heart and lung. In membranes from the heart (which contain mostly β₁-adrenergic receptors), the affinities of the derivatives and parent compounds were similar. By contrast, in membranes from the lung (which contain mostly β₂-adrenergic receptors), the derivatives were more potent than the parent compounds. Thus, the cardioselectivities of the p-aminobenzyl analogues 8a and 8b were about one-sixth those of the respective parents.