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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,*
Received: 29 November 2013; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

Ibacache JA, Delgado V, Benites J, Theoduloz C, Arancibia V, Muccioli GG, Valderrama JA. Synthesis, Half-Wave Potentials and Antiproliferative Activity of 1-Aryl-substituted Aminoisoquinolinequinones. Molecules. 2014; 19(1):726-739.

Chicago/Turabian Style

Ibacache, Juana A.; Delgado, Virginia; Benites, Julio; Theoduloz, Cristina; Arancibia, Verónica; Muccioli, Giulio G.; Valderrama, Jaime A. 2014. "Synthesis, Half-Wave Potentials and Antiproliferative Activity of 1-Aryl-substituted Aminoisoquinolinequinones." Molecules 19, no. 1: 726-739.



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