Basic ethers of cyclohexylphenols with beta-blocking activity: synthesis and pharmacological study of exaprolol.
The paper describes the preparation and study of the pharmacological properties of a series of derivatives with the general formula. (see article) where R is a cyclohexyl or cyclohexenyl radical and R1 is a hydrogen, methyl or cyclohexyl. The compounds with a single cycloaliphatic radical ortho to the basic chain, and in particular the one with a cyclohexyl (exaprolol), were found to be particularly active in blocking the beta-adrenergic receptors, as antiarrhythmics and local anesthetics, while the introduction of a second radical or the shift of the cycloaliphatic radical to meta or para position caused the said pharmacological activities to disappear almost entirely, with the exception of the local anesthetic action.
D000319:Adrenergic beta-Antagonists / Q000138:chemical synthesis / Q000633:toxicity; D000779:Anesthetics, Local; D000818:Animals; D000889:Anti-Arrhythmia Agents; D001794:Blood Pressure / Q000187:drug effects; D001980:Bronchi / Q000187:drug effects; D003510:Cyclohexanes / Q000494:pharmacology*; D006168:Guinea Pigs; D006339:Heart Rate / Q000187:drug effects; D066298:In Vitro Techniques; D007928:Lethal Dose 50; D008297:Male; D009119:Muscle Contraction / Q000187:drug effects; D009130:Muscle, Smooth / Q000187:drug effects; D009200:Myocardial Contraction / Q000187:drug effects; D010647:Phenyl Ethers / Q000494:pharmacology*; D011412:Propanolamines / Q000138:chemical synthesis / Q000494:pharmacology* / Q000633:toxicity; D011433:Propranolol / Q000494:pharmacology; D011817:Rabbits; D051381:Rats
D000319:Adrenergic beta-Antagonists; D000779:Anesthetics, Local; D000889:Anti-Arrhythmia Agents; D003510:Cyclohexanes; D010647:Phenyl Ethers; D011412:Propanolamines; D011433:Propranolol