N,N-disubstituted 4-amino-(6-methoxy)-3-phenyl-2H-naphtho [1,2-b]pyran-2-ones with antiarrhythmic, platelet antiaggregating and local anesthetic activities.
The synthesis of title compounds (VI) by 1,4-cycloaddition of phenylchloroketene to N,N-disubstituted (E)-2-aminomethylene-3,4-dihydro-(6-methoxy)-1(2H)naphthalenones, followed by dehydrochlorination with DBN and dehydrogenation with Pd/C of the resulting cycloadducts, is described. Some compounds (VI) showed antiarrhythmic activity in rats higher or like that of quinidine and platelet antiaggregating activity in vitro like that of acetylsalycilic acid, as well as moderate infiltration anesthesia in mice and weak hypotensive, bradicardic and antiinflammatory activities in rats.
Bargagna
A
A
Istituto di Scienze Farmaceutiche, Università di Genova, Italy.
Longobardi
M
M
Mariani
E
E
Schenone
P
P
Russo
S
S
Vilagliano
S
S
De Novellis
V
V
Marmo
E
E
D000779:Anesthetics, Local / Q000138:chemical synthesis*; D000818:Animals; D000889:Anti-Arrhythmia Agents / Q000138:chemical synthesis*; D001792:Blood Platelets / Q000187:drug effects; D001794:Blood Pressure / Q000187:drug effects; D006339:Heart Rate / Q000187:drug effects; D051379:Mice; D009279:Naphthacenes / Q000138:chemical synthesis* / Q000494:pharmacology; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis*; D011714:Pyrans / Q000138:chemical synthesis*; D011753:Pyrones / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship
D000779:Anesthetics, Local; D000889:Anti-Arrhythmia Agents; D009279:Naphthacenes; D010975:Platelet Aggregation Inhibitors; D011714:Pyrans; D011753:Pyrones