Naslov
Synthesis and anti-inflammatory activity of 8H-1- thia-8- aza-dibenzo[e, h]azulenes

Autori
Ozimec Landek, Ivana ; Pešić, Dijana ; Merćep, Mladen ; Stanić, Barbara ; Mesić, Milan

Izvornik
Journal of heterocyclic chemistry (0022-152X) 48 (2011), 4; 856-863

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
8H-1-thia-8-aza-dibenzo[e ; h]azulenes ; N-protection ; anti-inflammatory activity

Sažetak
Synthesis of a novel class of fused hetero- tetracyclic compounds, 8H-1-thia-8-aza-dibenzo[e, h]azulenes (VII), is described. Starting N- benzoyl-protected 5H-dibenzo[b, f]azepine (XI, PG = Bz) was oxidized to 5-benzoyl-10, 11- epoxy-10, 11-dihydro-5H-dibenzo[b, f]azepine (2) which subsequently rearranged in Lewis acid induced epoxide ring opening to give 5-benzoyl-5, 11- dihydro-10H- dibenzo[b, f]azepin-10-one (3). Vilsmeier reaction of 3 provided gama-chlorovinyl aldehyde 4 that readily cyclized with ethyl 2- mercaptoacetate to form dibenzazepino[4, 5]-fused thiophene structure 5. Further transformation of substituent at C-2 position of 5 and N- deprotection led to final aminoalkoxy derivatives 9. All compounds with tetracyclic skeleton were tested in vitro for their anti-inflammatory activity.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti

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