Aminoethers of 1,3,3-trimethyl-5-(phenylmethylene)-2-oxabicyclo[2.2.2]octan-6-h ydroxy imine with antiarrhythmic activity.
The synthesis of beta-dialkylaminoethyl ethers (III a-f) and gamma-dialkylaminopropyl ethers (III g-l) starting from 1,3,3-trimethyl-5-(phenylmethylene)-2-oxabicyclo[2.2.2]octan-6- hydroxyimine (II) is described. beta-Diisopropylaminoethyl ether (III b) and gamma-piperidinopropyl ether (III i) showed an antiarrhythmic activity in rats similar to that of quinidine. Moreover, a number of ethers (III) showed weak hypotensive and bradycardic activity in rats and moderate infiltration anesthesia in mice.
Mariani
E
E
Istituto di Scienze Farmaceutiche, Università di Genova, Italy.
Bargagna
A
A
Longobardi
M
M
Schenone
P
P
Russo
S
S
Filippelli
W
W
Molinario
L
L
Marmo
E
E
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*; D007097:Imines / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D051381:Rats; D013329:Structure-Activity Relationship
D000779:Anesthetics, Local; D000889:Anti-Arrhythmia Agents; D000959:Antihypertensive Agents; D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D007097:Imines