Esters of N-(2-hydroxy-1,1-dimethylethyl)-1,7,7-trimethylbicyclo[2.2.1] heptan-2-exo-amine with hypotensive activity.
The synthesis of title compounds by reaction of camphor nitrimine with 2-amino-2-methylpropanol, followed by NaBH4 reduction of the resulting imine to the aminoalcohol (III) and esterification of (III) with aliphatic and aromatic acyl chlorides in pyridine solution, is described. Phenyl carbamate (V) was also prepared by reaction of (III) with phenyl isocyanate. Some esters and (V) showed a moderate hypotensive activity in rats. Effects on heart rate and antiarrhythmic activity in rats, as well as infiltration anesthesia in mice, are also reported.
Bondavalli
F
F
Istituto di Scienze Farmaceutiche, Università di Genova, Italy.
Bruno
O
O
Ranise
A
A
Schenone
P
P
Susanna
V
V
Lisa
M
M
Maione
S
S
Marmo
E
E
D000588:Amines / Q000138:chemical synthesis* / Q000494:pharmacology; D000779:Anesthetics, Local / Q000138:chemical synthesis; D000818:Animals; D000889:Anti-Arrhythmia Agents / Q000138:chemical synthesis; D000959:Antihypertensive Agents / Q000138:chemical synthesis* / Q000494:pharmacology; 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; D006339:Heart Rate / Q000187:drug effects; D008297:Male; D051381:Rats
D000588:Amines; D000779:Anesthetics, Local; D000889:Anti-Arrhythmia Agents; D000959:Antihypertensive Agents; D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds