Synthesis of new N,N-disubstituted 4-amino-5,6-dihydro-3-phenyl-2H-thieno[2,3-h]-1-benzopyran-2-ones.
The synthesis of some N,N-disubstituted 4-amino-5,6-dihydro-3-phenyl-2H-thieno[2,3-h]-1-benzopyran-2-ones (4a-f), by reaction of phenylchloroketene with a series of N,N-disubstituted (E)-5-aminomethylene-6,7-dihydrobenzo[b]thiophen-4(5)-ones, followed by dehydrochlorination in situ of the primary adducts with DBN, is described. A moderate local anaesthetic activity was observed in the title compounds, particularly in 4e.
Longobardi
M
M
Dipartimento di Scienze Farmaceutiche dell'Università di Genova, Italy. longobar@unige.it
Mariani
E
E
Bargagna
A
A
Mazzeo
F
F
Vitelli
M R
MR
Giordano
L
L
Falcone
G
G
D000698:Analgesia; D000779:Anesthetics, Local / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051379:Mice; D051381:Rats; D013329:Structure-Activity Relationship
D000779:Anesthetics, Local; D000894:Anti-Inflammatory Agents, Non-Steroidal; D001578:Benzopyrans