Synthesis and cytotoxic activity of 11-nitro and 11-amino derivatives of acronycine and 6-demethoxyacronycine

Condensation of 2-chloro-3-nitrobenzoic acid with either 5-amino-7-methoxy- 2,2-dimethyl-2H-chromene or 5-amino-2,2-dimethyl-2H-chromene afforded diphe nylamines 14 and 15. Trifluoroacetic anhydride mediated cyclization gave th e corresponding acridones 16 and 17, which were subsequently N-methylated a nd reduced to 11-aminoacronycine and 11-amino-6-demethoxyacronycine. These two amino compounds, which gave stable water soluble salts, were 2- t o 3-fold more potent than acronycine or 6-demethoxyacronycine in inhibiting L1210 cell proliferation.