Reactions of vicinal aromatic dibromo derivatives Ia-d with the system copper(I) cyanide-tetramethylurea gave the vicinal dicyano derivatives IIa-d; products of partial substitution, Va-d, demethylation and deacetylation, IIIa-c, were also formed. The compounds IIIa-c were also prepared by direct demethylation of compounds IIa-c with the system anhydrous aluminium chloride-dichloroethane. The structures of selected compounds were determined by spectral methods. Compounds IIa-d have proved to have a moderate antineoplastic effect in animals with some transplantable experimental tumours.
The main objective of the present investigation was to screen a series of new benzo(c)fluorene compounds for in vitro activity. It can be stated that each of the 9 newly synthesized benzo(c)fluorene derivatives was about 10 times as active as tilorone. To elucidate the biochemical mode of action, the effects of 2 new compounds (13468 and 14200) on biosynthesis of macromolecules indicated by the incorporation rate of [14C]adenine (DNA, RNA), [14C]-thymidine (DNA), [14C]uridine (RNA) and [14C]valine (protein) were studied in concentration and time dependence. Both compounds inhibited the incorporation of the 4 precursors into the TCA-insoluble fraction of Ehrlich ascites carcinoma cells.
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