N-Substituted 1,7,7-trimethyl-2-piperidinobicyclo[2.2.1]hept-2-ene 5-carboxamides and 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 3-carboxamides with hypotensive and other activities.
The synthesis of N-substituted 1,7,7-trimethyl-2-piperidinobicyclo[2.2.1]hept-2-ene 3 carboxamides (II) by reaction of 1,7,7-trimethyl-2-piperidinobicyclo[2.2.1]hept-2-ene (I) with alkyl and aryl isocyanates, as well as the alkaline hydrolysis of (II) to N-substituted 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 3 carboxamides (III), are described. A number of compounds (II) and (III) showed strong hypotensive and bradycardiac activities in rats, as well as weak infiltration anesthesia and antiarrhythmic activity in mice. Antiacetylcholine activity in vitro is also reported.
D000109:Acetylcholine / Q000037:antagonists & inhibitors; D000779:Anesthetics, Local / Q000138:chemical synthesis; D000818:Animals; D000889:Anti-Arrhythmia Agents / Q000138:chemical synthesis; D000959:Antihypertensive Agents / Q000138:chemical synthesis*; D001794:Blood Pressure / Q000187:drug effects; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D006168:Guinea Pigs; D006339:Heart Rate / Q000187:drug effects; D066298:In Vitro Techniques; D051379:Mice; D010880:Piperidines / Q000138:chemical synthesis; D051381:Rats
D000779:Anesthetics, Local; D000889:Anti-Arrhythmia Agents; D000959:Antihypertensive Agents; D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D010880:Piperidines; D000109:Acetylcholine