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Molecules 2013, 18(8), 9818-9832; doi:10.3390/molecules18089818
Article

Eco-Friendly Synthesis and Antiproliferative Evaluation of Some Oxygen Substituted Diaryl Ketones

1, 1, 1,2, 1,2,* , 3, 1,2,4 and 1,2,5,*
1 Facultad de Ciencias de la Salud, Universidad Arturo Prat, Casilla 121, Iquique 1100000, Chile 2 Instituto de EtnoFarmacología (IDE), Universidad Arturo Prat, Casilla 121, Iquique 1100000, Chile 3 Bioanalysis and Pharmacology of Bioactive Lipids Laboratory, Louvain Drug Research Institute, Université Catholique de Louvain, 72 Avenue E. Mounier, BPBL 7201, 1200 Brussels, Belgium 4 Toxicology and Cancer Biology Research Group, Louvain Drug Research Institute, Université Catholique de Louvain, 73 Avenue E. Mounier, GTOX 7309, 1200 Brussels, Belgium 5 Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Santiago 6094411, Chile
* Authors to whom correspondence should be addressed.
Received: 26 June 2013 / Revised: 5 August 2013 / Accepted: 12 August 2013 / Published: 16 August 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

A broad variety of oxygen-substituted diaryl ketones has been synthesized by solar energy-induced Friedel Crafts acylations of 1,4-benzo- and 1,4-naphthoquinones with benzaldehydes. The in vitro antiproliferative properties of the photoproducts were assessed on prostate (DU-145), bladder (T24) and breast (MCF7) human-derived tumor cell lines and compared to non-tumor mouse fibroblasts (Balb/3T3). Among the tested compounds, it was found that those containing a 3,4,5-trimethoxyphenyl A-ring, such as 12 and 22 are more active on DU-145, with EC50 values of 1.2 and 5.9 μM, respectively. By comparing their effects on the three cancer cell lines, the analogue 22 has the best mean selective index (2.4).
Keywords: photo-Friedel Crafts acylation; diaryl ketones; green chemistry; antiproliferative activity photo-Friedel Crafts acylation; diaryl ketones; green chemistry; antiproliferative activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Arenas, P.; Peña, A.; Ríos, D.; Benites, J.; Muccioli, G.G.; Calderon, P.B.; Valderrama, J.A. Eco-Friendly Synthesis and Antiproliferative Evaluation of Some Oxygen Substituted Diaryl Ketones. Molecules 2013, 18, 9818-9832.

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