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Molecules 2012, 17(10), 11616-11629; doi:10.3390/molecules171011616
Article

Synthesis and Antitumor Evaluation of 6-Aryl-substituted benzo[j]phenanthridine- and Benzo[g]pyrimido[4,5-c]isoquinolinequinones

1, 2,3, 4, 1,3, 1,3 and 3,5,*
1 Facultad de Ciencias de la Salud, Universidad Arturo Prat, Casilla 121, Iquique 1100000, Chile 2 Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Santiago 8380492, Chile 3 Instituto de EtnoFarmacología (IDE), Universidad Arturo Prat, Casilla 121, Iquique 1100000, Chile 4 Facultad de Ciencias de la Salud, Universidad de Talca, Talca 3460000, Chile 5 Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Santiago 6094411, Chile
* Author to whom correspondence should be addressed.
Received: 10 September 2012 / Revised: 23 September 2012 / Accepted: 25 September 2012 / Published: 28 September 2012
(This article belongs to the Section Organic Synthesis)
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Abstract

A variety of novel 6-arylsubstituted benzo[j]phenanthridine- and benzo[g]-pyrimido[4,5-c]isoquinolinequinones were synthesized from 1,4-naphthoquinone, aryl-aldehydes and enaminones via a two-step synthetic approach. The cytotoxic activity of the aminoquinone derivatives was evaluated in vitro against one normal cell line (MRC-5 lung fibroblasts) and three human cancer cell lines (AGS human gastric adenocarcinoma; SK-MES-1 human lung cancer cells, and J82 human bladder carcinoma) in 72-h drug exposure assays using the MTT colorimetric method. Structure–activity relationships within the series of angular quinones reveal that the insertion of pyrrol-2-yl and furan-2-yl groups at the 6-position is more significant for the increase of the potency and selectivity index of the pharmacophores.
Keywords: N-heterocyclic quinones; enaminones; cytotoxicity; SAR analysis N-heterocyclic quinones; enaminones; cytotoxicity; 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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Iribarra, J.; Vásquez, D.; Theoduloz, C.; Benites, J.; Ríos, D.; Valderrama, J.A. Synthesis and Antitumor Evaluation of 6-Aryl-substituted benzo[j]phenanthridine- and Benzo[g]pyrimido[4,5-c]isoquinolinequinones. Molecules 2012, 17, 11616-11629.

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