Ureas and amides derived from N-(5-norbornen-2-ylmethyl) bornan-2-exo-amine with antiarrhythmic and other activities.
The synthesis of title compounds by reaction of camphor nitrimine with (5-norbornen-2-yl)methylamine, followed by NaBH4 reduction of the resulting imine to N-substituted isobornylamine (IV) and reaction of (IV) with alkyl and aryl isocyanates or acyl chlorides, is described. Some ureas and amides are endowed with antiarrhythmic activity in rats superior or comparable to that of quinidine, whereas benzamide (V o) showed an appreciable hypoglycemic activity in mice. Moreover, compounds (V) exhibited in general moderate hypotensive, bradycardic and antiinflammatory activities in rats, as well as a weak infiltration anesthesia in mice.
Ranise
A
A
Istituto di Scienze Farmaceutiche, Università di Genova, Italy.
Bondavalli
F
F
Schenone
P
P
Angrisani
M
M
Lisa
M
M
Marrazzo
R
R
Marmo
E
E
D000577:Amides / Q000138:chemical synthesis*; D000779:Anesthetics, Local / Q000138:chemical synthesis; D000818:Animals; D000889:Anti-Arrhythmia Agents / Q000138:chemical synthesis*; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis; D001794:Blood Pressure / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D006339:Heart Rate / Q000187:drug effects; D007004:Hypoglycemic Agents / Q000138:chemical synthesis; D051379:Mice; D009636:Norbornanes / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D014508:Urea / Q000031:analogs & derivatives*
D000577:Amides; D000779:Anesthetics, Local; D000889:Anti-Arrhythmia Agents; D000893:Anti-Inflammatory Agents; D007004:Hypoglycemic Agents; D009636:Norbornanes; D014508:Urea