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 diphenylamines 14 and 15. Trifluoroacetic anhydride mediated cyclization gave the corresponding acridones 16 and 17, which were subsequently N-methylated and reduced to 11-aminoacronycine and 11-amino-6-demethoxyacronycine. These two amino compounds, which gave stable water soluble salts, were 2- to 3-fold more potent than acronycine or 6-demethoxyacronycine in inhibiting L1210 cell proliferation.
Elomri
A
A
Laboratoire de Pharmacognosie de l'Université de Rouen-Haute Normandie, Faculté de Pharmacie, France.
Michel
S
S
Koch
M
M
Seguin
E
E
Tillequin
F
F
Pierré
A
A
Atassi
G
G
D000175:Acronine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D007939:Leukemia L1210 / Q000473:pathology; D051379:Mice; D013057:Spectrum Analysis; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
C402803:11-amino-6-demethoxyacronycine; C402802:11-aminoacronycine; D000175:Acronine