1. Natural and Synthetic Furanones with Anticancer Activity
- Author
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Véronique Mathieu, Patrizia Scafato, Stefano Superchi, Wanda D'Amico, Lucia Maddau, Laura Pisani, Alessio Cimmino, Antonio Evidente, Aude Ingels, Robert Kiss, Cimmino, Alessio, Scafato, Patrizia, Mathieu, Veronique, Ingels, Aude, D'Amico, Wanda, Pisani, Laura, Maddau, Lucia, Superchi, Stefano, Kiss, Robert, and Evidente, Antonio
- Subjects
Diplodia corticola ,Diplodia corticola, Furanones, Sapinofuranones, Diplofuranone, Diplobifuranylones, Enantioselective synthesis, Analogues, In Vitro anticancer activity ,Stereochemistry ,Antineoplastic Agents ,Growth inhibitory ,Plant Science ,Ring (chemistry) ,Inhibitory postsynaptic potential ,01 natural sciences ,Ascomycota ,Cell Line, Tumor ,Drug Discovery ,Side chain ,Humans ,Furans ,Pharmacology ,Molecular Structure ,010405 organic chemistry ,Chemistry ,Enantioselective synthesis ,Stereoisomerism ,General Medicine ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,Drug Screening Assays, Antitumor ,Cancer cell lines ,In vitro growth - Abstract
This paper describes the enantioselective synthesis of analogues of sapinofuranones A and B, namely 5-substitutes dihydro- and 5 H-furan-ones, and their in vitro growth inhibitory activity against six cancer cell lines in comparison with fungal furanones such as diplofuranone A, diplobifuranylones A and B, as well as ( S,S)-enantiomer of sapinofuranone B. The compounds under study displayed weak if any in vitro growth inhibitory activity against the analysed cancer cell lines. However, it seems that among dihydro- and 5 H-furan-ones bearing a 1-hydroxypentyl side chain, the stereochemistry of the furanone ring and that of hydroxylated methine could modify the in vitro growth activity of these compounds. The natural furanones that showed a different unsaturated chain at C-4 or rearranged into a dihydrofuran ring appeared to be inactive in terms of growth inhibitory activity, e.g. displaying growth inhibitory concentration at 50% (GI50) > 100 μM in all six cancer cell lines analysed.
- Published
- 2016
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