Synthesis and beta-adrenergic blocking activity of a novel class of aromatic oxime ethers.
PMID 22751 · Journal of medicinal chemistry · 1977 · DOI 10.1021/jm00222a023
Authors: G Leclerc; A Mann; C G Wermuth; N Bieth; J Schwartz
Abstract
A new series of beta-adrenergic blocking amines containing an oximino-propanolic chain linked to an aromatic nucleus was synthesized. Most of the derivatives are characterized by beta2-selectivity. The structure-activity relationship are discussed. One of the compounds, selected for further studies, was more active on the trachea than on the atria of guinea pig, 155 times in vitro and 26 times in vivo. In comparison, butoxamine's beta2-selectivity is 13 in vitro and only 2 in vivo. With a series of 30 acetophenone oxime derivatives, no quantitative structure-activity relationships could be detected.
Adrenergic beta-Antagonists; Airway Resistance; Animals; Guinea Pigs; Heart Rate; In Vitro Techniques; Isoproterenol; Muscle Contraction; Muscle, Smooth; Oximes; Structure-Activity Relationship
Cite
G Leclerc; A Mann; C G Wermuth; N Bieth; J Schwartz. Synthesis and beta-adrenergic blocking activity of a novel class of aromatic oxime ethers. Journal of medicinal chemistry (1977). PMID 22751. DOI 10.1021/jm00222a023.