In the present study, the synthesis and cytotoxic effect of six stilbenes and three oxepine derivatives against twocancerous–HeLa and U87, and two normal–EUFA30 and HEK293 cell lines has been reported. The results ofcytotoxic assay andflow cytometry analysis revealed that compounds 9-nitrobenzo[b]naphtho[1,2-f]oxepine(4), (E)-3,3′,4,4′,5,5′-hexamethoxystilbene (6) and 4-hydroxy-2′,4′-dinitrostilbene (8) were the most active andtheir interaction with tubulin (crystal structure from PDB) has been analyzed by computer molecular modeling.Molecular docking of these compounds on colchicine binding site of the tubulin indicates the interaction of (4),(6) and (8) with tubulin. The compound (4) could interact stronger with tubulin, relative to colchicine, however,with no selectivity of action against cancer and normal cells. Conversely, compounds (6) and (8) interact moreweakly with tubulin, relative to colchicine but they act more selectively towards cancerous versus normal celllines. Obtained results proved that the compounds that are the most active against cancerous cells operatethrough tubulin binding
