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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 (CC BY 3.0).
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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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