Naphthannelated azepinones: synthesis and antitumor activity

5 H-Benzo[b]naphth[2,3-e]azepine-6,13-diones 4a, 4b and 4 H-naphtho[2,3-e]t hieno[3,2-b]azepine-5,12-dione (6) were prepared by aldol condensation of p hthalic dialdehyde (3) with the fused azepinediones 2a, 2b and 5, respectiv ely. The Schmidt reaction of naphthacene-5,12-quinone (7) yielded 6 H-benzo [e]naphth[2,3-b]azepine-7,12-dione (10). Several derivatives of the heteroc yclic basic scaffolds 4, 6 and 10 were prepared by standard procedures, e.g . Grignard reaction, deoxygenation with triethylsilane, and sodium borohydr ide reduction. Evaluation of the synthesized compounds in the NCl in vitro cell line screening revealed a modest antitumor activity without marked cel l line selectivity for the majority of the derivatives. The 2-bromo-5H-benz o[b]naphth[2,3-e]azepin-6(13 H)-one (19) was the only representative in thi s series exhibiting a noteworthy growth inhibitory effect for human tumor c ells.