Aminoethers of (+)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-hydroxyimine with hypotensive activity.
The synthesis of beta-dialkylaminoethyl ethers (II a-f) and gamma-dialkylaminopropyl ethers (II g-i), as well as of aryl carbamates (III 1, m), starting from (+)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-hydroxyimine (I), is described. beta-Dimethylaminoethyl ether (II a) showed a remarkable hypotensive and bradycardic activity in rats; moreover, nearly all compounds (II) and (III) exhibited a weak antiarrhythmic activity in rats. Infiltration anesthesia in mice, beta-blocking activity in dogs and antiacetylcholine activity in vitro are also reported.
Bondavalli
F
F
Bruno
O
O
Ranise
A
A
Schenone
P
P
Filippelli
W
W
Rossi
F
F
Gentile
B
B
Matera
C
C
Marmo
E
E
D000109:Acetylcholine / Q000037:antagonists & inhibitors; D000157:Aconitine / Q000037:antagonists & inhibitors; D000319:Adrenergic beta-Antagonists / Q000138:chemical synthesis; 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* / Q000494:pharmacology; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D004285:Dogs; D006339:Heart Rate / Q000187:drug effects; D007097:Imines / Q000138:chemical synthesis* / Q000494:pharmacology; D008297:Male; D051379:Mice; D051381:Rats
D000319:Adrenergic beta-Antagonists; D000779:Anesthetics, Local; D000889:Anti-Arrhythmia Agents; D000959:Antihypertensive Agents; D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D007097:Imines; D000109:Acetylcholine; D000157:Aconitine