Esters of N-methyl-N-(2-hydroxyethyl or 3-hydroxypropyl)-1,3,3-trimethylbicyclo [2.2.1]heptan-2-endo-amine with hypotensive activity.
The synthesis of title compounds by reaction of fenchone nitrimine with 2-aminoethanol and 3-aminopropanol, followed by stereospecific NaBH4 reduction of the resulting imines, Eschweiler-Clarke reductive methylation and esterification with aliphatic and aromatic acyl chlorides is described. Some esters showed an appreciable hypotensive activity in rats. Effects on heart rate and antiarrhythmic activity in rats, as well as infiltration anesthesia in mice, are also reported.
D000779:Anesthetics, Local / Q000138:chemical synthesis; D000818:Animals; D000889:Anti-Arrhythmia Agents / Q000138:chemical synthesis; 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; D008297:Male; D051379:Mice; D051381:Rats
D000779:Anesthetics, Local; D000889:Anti-Arrhythmia Agents; D000959:Antihypertensive Agents; D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds