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Synthesis, antitumor activity and docking of 2,3-(substituted)-1,4-naphthoquinone derivatives containing nitrogen, oxygen and sulfur

Delarmelina, Maicon, Daltoé, Renata D., Cerri, Murilo F., Madeira, Klesia P., Rangel, Leticia B. A., Lacerda Júnior, Valdemar, Romão, Wanderson, Taranto, Alex G. and Greco, Sandro J. 2015. Synthesis, antitumor activity and docking of 2,3-(substituted)-1,4-naphthoquinone derivatives containing nitrogen, oxygen and sulfur. Journal of the Brazilian Chemical Society 26 (9) , pp. 1804-1816. 10.5935/0103-5053.20150157

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Abstract

Eleven 2,3-(substituted)-1,4-naphthoquinone derivatives were synthesized in yields ranging from 52-89%. These derivatives were evaluated for their cytotoxic effects on human lungs (H460), triple-negative breast (MDA-MB-231) and ovarian (A2780) cancer cell lines. Compounds 5f and 8 showed IC50 values of 3.048 × 10-5 mol L-1 and 4.24 × 10-6 mol L-1 for H460; 5c and 8 showed IC50 values of 2.16 × 10-5 mol L-1 and 1.60 × 10-5 mol L-1 for MDA-MB-231, and 5g and 8 showed IC50 values of 2.68 × 10-6 mol L-1 and 3.89 × 10-6 mol L-1 for A2780. Additionally, we conducted a docking study with the four most active compounds and the therapeutic targets PI3K and topoisomerase II showing the pharmacophoric conformation of these compounds.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Publisher: Sociedade Brasileira de Química, SBQ
ISSN: 0103-5053
Last Modified: 03 Jun 2019 10:30
URI: http://orca.cf.ac.uk/id/eprint/122293

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