ABSTRACT
May's benzomorphan synthesis leads not only to the alpha or cis isomer and the beta or trans isomer but also to a position isomer hereinafter called the gamma isomer. The structure and synthesis of this isomer are described. Biological activities of the alpha and gamma isomers are compared.
Subject(s)
Benzomorphans , Morphinans , Animals , Benzomorphans/analogs & derivatives , Benzomorphans/pharmacology , Chemical Phenomena , Chemistry , Isomerism , Morphinans/analogs & derivatives , Morphinans/pharmacology , Narcotic Antagonists , Narcotics , Rats , Structure-Activity RelationshipABSTRACT
The preparation of various esters of N-tert-butylarterenol is described. Esterification of the phenolic OH groups has increased bioavailability, prolonged bronchodilation, and reduced tachycardia. The substitution of aromatic esters compared with simple aliphatic esters improved markedly these pharmacological properties. Of a number of esters tested, compound 45 (bitolterol) demonstrated the most favorable pharmacological properties as a bronchodilator. Its long duration of action and significant bronchodilator-cardiovascular separation are briefly described.
