Conformational effects on the activity of drugs. 10. Synthesis, conformation, and pharmacological properties of 1-(2,5-dimethoxyphenyl)-2-aminoethanols and their morpholine analogs

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Abstract
In order to obtain a better understanding of the effects that structural parameters have on the changes of adrenergic activity when 1-aryl-2-aminoethanol derivatives are converted into their corresponding 2-arylmorphine cyclic analogs, 1-(2,5-dimethoxyphenyl)-2-aminoethanol derivatives 5-7 and their morpholine analogs 8-10 [2-(2,5-dimethoxyphenyl)morpholine derivatives]. The preferred conformation of amino alcohols and their cyclic analogs were determined through a 1H NMR and IR study. Compound 5 showed .alpha.-stimulating and .alpha.-blocking activity on rat vas deferens, the effect depending on the concentration employed; on the same isolated tissue, N-isopropyl derivative 7 and the morpholine analogs 8-10 exhibited only .alpha.-blocking activity. As for the .beta.-adrenergic activity, only the open-chain compound 7 possessed a moderate blocking effect on isolated guinea pig atria. The changes of pharmacological activity involved in the transformation of the adrenergic drugs into their morpholine analogs are evidently influenced more by characteristic features of the aromatic moiety than by the ethanolamine or propanolamine structure of the drugs.

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