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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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