New 2-Acetyl-3-aminophenyl-1,4-naphthoquinones: Synthesis and Antiproliferative Activities on Breast and Prostate Human Cancer Cells.

The reaction of 2-acyl-1,4-naphthoquinones with ,-dimethylaniline and 2,5-dimethoxyaniline, promoted by catalytic amounts of CeCl·7HO under "open-flask" conditions, produced a variety of 2-acyl-3-aminophenyl-1,4-naphthoquinones structurally related to the cytotoxic 2-acetyl-3-phenyl-1,4-naphthoquinone, an inhibitor of the heat shock chaperone protein Hsp90. The members of the 2-acyl-3-aminophenyl-1,4-naphthoquinone series were isolated in good yields (63-98%). The cyclic voltammograms of the 2-acyl-3-aminophenyl-1,4-naphthoquinone exhibit two one-electron reduction waves to the corresponding radical-anion and dianion and two quasireversible oxidation peaks.