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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

Jennyfer Iribarra ¹ , David Vásquez ^2,3 , Cristina Theoduloz ⁴ , Julio Benites ^1,3 , David Ríos ^1,3  and Jaime A. Valderrama ^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; in revised form: 23 September 2012 / Accepted: 25 September 2012 / Published: 28 September 2012

(This article belongs to the Section Organic Synthesis)

Download PDF Full-Text [353 KB, uploaded 28 September 2012 15:54 CEST]

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

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