SYNTHESIS AND BETA-ADRENERGIC ACTIVITY OF A SERIES OF 3-(SUBSTITUTED-BENZYLIDENEAMINOXY)PROPANOLAMINE DERIVATIVES

In an attempt to change the beta-adrenergic properties of completely a liphatic 3-(methyleneaminoxy)propanolamine derivatives, from antagonis t to agonist, while still retaining the beta(2)-selectivity, we descri bed, in a previous paper, the synthesis of a series of such derivative s possessing a hydroxy or methoxy group linked to the aliphatic substi tuent present on the oximic carbon. However, pharmacological tests ind icated that these compounds maintain the competitive antagonism on bet a receptors. In this paper, the synthesis and the results of functiona l tests on isolated preparations are reported for a new series of 3-(s ubstituted-benzylideneaminoxy)propanolamine derivatives in which eithe r the hydroxy or the methoxy group is linked to a phenyl ring present on the oximic carbon. The results obtained are then discussed, taking into account the conformational and reactivity properties of these com pounds, determined by means of theoretical calculations.