N-Phenyl-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-cis-amine derivatives with hypotensive and other activities.
The synthesis of N-phenyl-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-cis-amine (III) starting from 6-nitrimino-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, as well as of a series of amides (IV) and ureas (VI) derived from (III), is described. A number of compounds (IV) showed strong hypotensive and bradycardic activity in rats, whereas the urea (IVb) showed infiltration anesthesia in mice similar to that of lidocaine. Antiarrhythmic activity in mice and antiacetylcholine activity in vitro are also reported.
D000109:Acetylcholine / Q000037:antagonists & inhibitors; D000779:Anesthetics, Local / Q000138:chemical synthesis; D000818:Animals; D000959:Antihypertensive Agents / Q000138:chemical synthesis*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D006339:Heart Rate / Q000187:drug effects; D051379:Mice; D051381:Rats; D013997:Time Factors
D000779:Anesthetics, Local; D000959:Antihypertensive Agents; D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D000109:Acetylcholine