Naslov
Synthesis of 2-formyl-1-aza-dibenzo[e, h]azulenes

Autori
Pešić, Dijana ; Ozimec Landek, Ivana ; Čikoš, Ana ; Metelko, Biserka ; Gabelica, Vesna ; Stanić, Barbara ; Merćep, Mladen ; Mesić, Milan

Izvornik
Journal of Heterocyclic Chemistry (0022-152X) 44 (2007), 5; 1129-1133

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

Ključne riječi
dibenzoazulenes ; anti-inflammatory compounds ; TNF-alpha

Sažetak
Synthesis of a novel heterocyclic class of compounds, 1-aza-dibenzo(e, h)azulenes derived from dibenzo(b, f)oxepin, its 8-chloro analogue and dibenzo(b, f)thiepin, respectively, is described. Aldol condensation of the starting ketones 4a-c with (dimethyl-hydrazono)-acetaldehyde affords dydrazonoethylidene derivatives 5a-c, which on reduction with sodium dithionite and subsequent cyclization provide target tetracyclic 1-aza-dibenzo(e, h)azulenes 6a-c. Regiospecific formylation of 6a-c with Vilsmeier reagent leads to 2-formyl derivatives 7a-c. A series of derivatives 6a-c and 7a-c was tested for antiinflammatory activity as potential inhibitors of tumor necrosis factor alpha (TNF-a) production in vitro.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija, Temeljne medicinske znanosti

POVEZANOST RADA