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Analogues of cytotoxic squamocin using reliable reactions: new insights into the reactivity and role of the α,β-unsaturated lactone of the annonaceous acetogenins |
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| Authors: | Romain A. Duval Vanessa Romero Guy Lewin Ulrich Brandt |
| Affiliation: | a Laboratoire de Pharmacognosie associé au CNRS, UMR 8076, Centre d'Études Pharmaceutiques, Université Paris-Sud 11, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry CEDEX, France b Departamento de Farmacología, Laboratorio de Farmacognosia, Facultad de Farmacia, Universidad de Valencia, 46100 Burjassot, Valencia, Spain c Zentrum der Biologischen Chemie, Fachbereich Medizin, Universität Frankfurt, Theodor-Stern-Kai 7, Haus 26, D-60590 Frankfurt am Main, Germany |
| Abstract: | A small library of squamocin analogues has been prepared and screened biologically (cytotoxicity, inhibition of mitochondrial complex I and complex III). To centre diversity on a crucial part of the molecule (i.e., the α,β-unsaturated lactone), an original and reliable lactone opening reaction has been discovered and exploited among other efficient reactions. |
| Keywords: | Annonaceous acetogenins Squamocin Unsaturated lactone Chemistry in water Diels-Alder Click chemistry |
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