N-monosubstituted urethanes and esters of 6-cis-dimethylamino-1,3,3-trimethyl-2-oxabicyclo-[2.2.2]octan-5-trans-ol with hypotensive and other activities.
The synthesis of 6-cis-dimethylamino-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-5-trans-ol (III) starting from 1,3,3-trimethyl-6-nitrimino-2-oxabicyclo[2.2.2]octane is described. Starting from aminoalcohol (III), a series of N-substituted urethanes (IV) and esters (V), as well as the rigid analogue of acetylcholine (VII), were prepared. A number of compounds (V) and particularly (IV) showed remarkable hypotensive and bradycardic activities in rats, whereas the p-aminobenzoate (V h) showed infiltration anesthesia in mice comparable to that of lidocaine. Antiarrhythmic activity in mice and antiacetylcholine activity in vitro are also reported.
D000109:Acetylcholine / Q000037:antagonists & inhibitors; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000494:pharmacology; D000779:Anesthetics, Local / Q000138:chemical synthesis; D000818:Animals; D000889:Anti-Arrhythmia Agents / Q000138:chemical synthesis; D000959:Antihypertensive Agents / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D006439:Hemodynamics / Q000187:drug effects; D051379:Mice; D000442:Octanols / Q000138:chemical synthesis / Q000494:pharmacology; D051381:Rats
D000605:Amino Alcohols; D000779:Anesthetics, Local; D000889:Anti-Arrhythmia Agents; D000959:Antihypertensive Agents; D000442:Octanols; D000109:Acetylcholine