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Microwave Assisted Synthesis of 2,2'-Arylene-substituted Bis(4H-3,1-Benzoxazin-4-one) Derivatives Using the Complex Cyanuric Chloride/N,N-Dimethylformamide
Molecules 2012, 17(10), 11616-11629; doi:10.3390/molecules171011616

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,*
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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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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