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

Rios, David; Valderrama, Jaime A.; Cautin, Miriam; Tapia, Milko; Salas, Felipe; Guerrero-Castilla, Angelica; Muccioli, Giulio G.; Calderon, Pedro Buc; Benites, Julio

Abstract

The reaction of 2-acyl-1,4-naphthoquinones withN,N-dimethylaniline and 2,5-dimethoxyaniline, promoted by catalytic amounts of CeCl3 center dot 7H(2)O 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. The first and second half-wave potential values (E1/2) of the members of the series are sensitive to the push-pull electronic effects of the substituents in the naphthoquinone scaffold. Furthermore, thein vitroantiproliferative properties of these new quinones were evaluated on two human cancer cells DU-145 (prostate) and MCF-7 (mammary) and a nontumorigenic HEK-293 (kidney) cell line, using the MTT colorimetric method. Two members, within the series, exhibited interesting cytotoxic activities on human prostate and mammary cancer cells.

Más información

Título según WOS: New 2-Acetyl-3-aminophenyl-1,4-naphthoquinones: Synthesis and In Vitro Antiproliferative Activities on Breast and Prostate Human Cancer Cells
Título de la Revista: OXIDATIVE MEDICINE AND CELLULAR LONGEVITY
Volumen: 2020
Editorial: HINDAWI LTD
Fecha de publicación: 2020
DOI:

10.1155/2020/8939716

Notas: ISI