2H-[1]benzothiepino [5,4-b]pyran derivatives with local anesthetic and antiarrhythmic activities.
The synthesis of some N,N-disubstituted 4-amino-5,6-dihydro-3-phenyl-2H-[1]benzothiepino [5,4-b]pyran-2-ones by reaction of phenylchloroketene with a series of N,N-disubstituted (E)-4-aminomethylene-3,4-dihydro-1-benzothiepin-5(2H)-ones, followed by dehydrochlorination of the primary adducts with DBN, is described. The 4-methylphenylamino derivative showed a local anesthetic activity in mice superior to that of lidocaine and the 4-morpholino derivative showed an antiarrhythmic activity in rats comparable to that of quinidine.
Istituto di Farmaceutiche dell'Università, Genova, Italy.
M
M
Longobardi
A
A
Bargagna
E
E
Mariani
P
P
Schenone
S
S
Vitagliano
L
L
Stella
A
A
Di Sarno
E
E
Marmo
D000779:Anesthetics, Local / Q000138:chemical synthesis*; D000818:Animals; D000889:Anti-Arrhythmia Agents / Q000138:chemical synthesis*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis; D000959:Antihypertensive Agents / Q000138:chemical synthesis; D001582:Benzothiepins / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D010974:Platelet Aggregation / Q000187:drug effects; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis; D011714:Pyrans / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D011930:Reaction Time / Q000187:drug effects; D013055:Spectrophotometry, Infrared; D013917:Thrombin / Q000494:pharmacology
D000779:Anesthetics, Local; D000889:Anti-Arrhythmia Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D000959:Antihypertensive Agents; D001582:Benzothiepins; D010975:Platelet Aggregation Inhibitors; D011714:Pyrans; D013917:Thrombin