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Antitumor Activity of Some Prenylated Xanthones
Centro de Química Medicinal da Universidade do Porto (CEQUIMED-UP), Faculdade de Farmácia, Universidade do Porto, Rua Aníbal Cunha 164, 4050-047 Porto, Portugal
Departamento de Química & QOPNA, Universidade de Aveiro, Campus Universitário de Santiago, 3810-193 Aveiro, Portugal
Serviço de Microbiologia, Faculdade de Farmácia, Universidade do Porto, Rua Aníbal Cunha 164, 4050-047 Porto, Portugal
Serviço de Química Orgânica, Faculdade de Farmácia, Universidade do Porto, Rua Aníbal Cunha 164, 4050-047 Porto, Portugal
* Author to whom correspondence should be addressed.
Received: 1 July 2009; in revised form: 29 July 2009 / Accepted: 10 August 2009 / Published: 11 August 2009
Abstract: Pyranoxanthones 6-8 were obtained by dehydrogenation of the respective dihydropyranoxanthones 3-5 with DDQ in dry dioxane. Two prenylated xanthones 10,11 were obtained from the reaction of 1-hydroxyxanthone (9) with prenyl bromide in alkaline medium, or by condensation of xanthone 9 with isoprene in the presence of orthophosphoric acid. The structural elucidation of the two new compounds 6,11, as well as an update of data for the already described prenylated derivatives 7,8,10 were accomplished by IR, UV, HRMS and NMR (1H, 13C, HSQC and HMBC) techniques. The effect of the prenylated xanthone derivatives on the in vitro growth of human tumor cell lines MCF-7 (breast adenocarcinoma) and NCI-H460 (non-small cell lung cancer) is also reported. Compounds 10 and 11 have been found to exhibit a moderate growth inhibitory activity against the MCF-7 cell line.
Keywords: xanthones; prenylation; dehydrogenation; antitumor activity; NMR spectroscopy
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MDPI and ACS Style
Castanheiro, R.A.; Silva, A.M.; Campos, N.A.; Nascimento, M.S.; Pinto, M.M. Antitumor Activity of Some Prenylated Xanthones. Pharmaceuticals 2009, 2, 33-43.
Castanheiro RA, Silva AM, Campos NA, Nascimento MS, Pinto MM. Antitumor Activity of Some Prenylated Xanthones. Pharmaceuticals. 2009; 2(2):33-43.
Castanheiro, Raquel A.; Silva, Artur M.; Campos, Naïr A.; Nascimento, Maria S.; Pinto, Madalena M. 2009. "Antitumor Activity of Some Prenylated Xanthones." Pharmaceuticals 2, no. 2: 33-43.