N-Monosubstituted urethanes of 6-cis-dialkylamino-1,3,3-trimethyl-2-oxabicyclo [2.2.2] octan-5-trans-ols with hypotensive and other activities.
The synthesis of three series of N-monosubstituted urethanes of 6-cis-dialkylamino-1,3,3-trimethyl-2-oxabicyclo [2.2.2] octan-5-transols (IV), (V) and (VI) (dialkylamino = pyrrolidino, piperidino, morpholino) by reaction of the corresponding aminoalcohols with alkyl or aryl isocyanates, is described. A number of compounds (IV) and (V) showed remarkable hypotensive and bradycardic activity in rats, whereas (IV c) showed infiltration anesthesia and (IV n) antiarrhythmic activity in mice comparable to those of lidocaine. Antiacetylcholine activity in vitro is also reported.
D000109:Acetylcholine / Q000037:antagonists & inhibitors; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000494:pharmacology; D000777:Anesthetics / Q000138:chemical synthesis; D000818:Animals; D000889:Anti-Arrhythmia Agents / Q000138:chemical synthesis; D000959:Antihypertensive Agents / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D006339:Heart Rate / Q000187:drug effects; D051379:Mice; D014520:Urethane / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology
D000605:Amino Alcohols; D000777:Anesthetics; D000889:Anti-Arrhythmia Agents; D000959:Antihypertensive Agents; D014520:Urethane; D000109:Acetylcholine