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Molecules 2014, 19(1), 726-739; doi:10.3390/molecules19010726
Article

Synthesis, Half-Wave Potentials and Antiproliferative Activity of 1-Aryl-substituted Aminoisoquinolinequinones

1,2,* , 1, 3,4, 5, 1, 6 and 1,3,4,*
1 Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Santiago 6094411, Chile 2 Facultad de Química y Biología Universidad de Santiago de Chile, Alameda 3363, Casilla 40, Santiago 9170022, Chile 3 Facultad de Ciencias de la Salud, Universidad Arturo Prat, Casilla 121, Iquique 1100000, Chile 4 Instituto de EtnoFarmacología (IDE), Universidad Arturo Prat, Casilla 121, Iquique 1100000, Chile 5 Facultad de Ciencias de la Salud, Universidad de Talca, Talca 3460000, Chile 6 Bioanalysis and Pharmacology of Bioactive Lipids Laboratory, Louvain Drug Research Institute, Université Catholique de Louvain, 72 Avenue E. Mounier, BPBL 7201, Brussels 1200, Belgium
* Authors to whom correspondence should be addressed.
Received: 29 November 2013 / Revised: 30 December 2013 / Accepted: 31 December 2013 / Published: 8 January 2014
(This article belongs to the Section Organic Synthesis)
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Abstract

The synthesis of a variety of 1-aryl-7-phenylaminoisoquinolinequinones from 1,4-benzoquinone and arylaldehydes via the respective 1-arylisoquinolinequinones is reported. The cyclic voltammograms of the new compounds exhibit two one-electron reduction waves to the corresponding radical-anion and dianion and two quasi-reversible oxidation peaks. The half-wave potential values (EI½) of the members of the series have proven sensitive to the electron-donor effect of the aryl group (phenyl, 2-thienyl, 2-furyl) at the 1-position as well as to the phenylamino groups (anilino, p-anisidino) at the 7-position. The antiproliferative activity of the new compounds was evaluated in vitro using the MTT colorimetric method against one normal cell line (MRC-5 lung fibroblasts) and two human cancer cell lines: AGS human gastric adenocarcinoma and HL-60 human promyelocytic leukemia cells in 72-h drug exposure assays. Among the series, compounds 5a, 5b, 5g, 5h, 6a and 6d exhibited interesting antiproliferative activities against human gastric adenocarcinoma. The 1-arylisoquinolinequinone 6a was found to be the most promising active compound against the tested cancer cell lines in terms of IC50 values (1.19; 1.24 µM) and selectivity index (IS: 3.08; 2.96), respect to the anti-cancer agent etoposide used as reference (IS: 0.57; 0.14).
Keywords: isoquinolinequinones; enaminones; half-wave potential; antiproliferative activity; SAR analysis isoquinolinequinones; enaminones; half-wave potential; antiproliferative activity; SAR analysis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Ibacache, J.A.; Delgado, V.; Benites, J.; Theoduloz, C.; Arancibia, V.; Muccioli, G.G.; Valderrama, J.A. Synthesis, Half-Wave Potentials and Antiproliferative Activity of 1-Aryl-substituted Aminoisoquinolinequinones. Molecules 2014, 19, 726-739.

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