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Synthèse de pyrroles polysubstitués par cyclisation à l'or : évaluation de l'activité de 3-arylpyrroles sur les microtubules

Abstract : A family of 3-arylpyrroles named pyakols have shown antimitotic properties on murine cell lines, displaying in particular an effect on microtubules. Given the interest of these properties in cancerology, this work is focused on these heterocycles. The objective of the first part was to develop a synthetic strategy based on the gold-catalysed cyclisation of α-amino-ynols intermediates in order to access the lead (Pyakol I). Then, the evaluation of the biological activity of this molecule on the cell cycle and on the cytoskeleton of various human tumoral cell lines was carried out. The first results revealed an original effect on the organization of the microtubules network and the positioning of the mitotic spindle. The developed strategy was then validated by modulating the 3-arylpyrrole moiety on diverse positions, and used for the synthesis of labelled derivatives. The second part of this manuscript focused on the development of a methodology to synthesize new polysubstituted 3-trifluoromethylpyrroles, based on the gold-catalyzed cyclisation reaction. Using trifluoroacetaldehyde as building-block, various trifluoromethylated pyrroles were obtained in mild conditions with good yields.
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Benjamin Guieu. Synthèse de pyrroles polysubstitués par cyclisation à l'or : évaluation de l'activité de 3-arylpyrroles sur les microtubules. Catalyse. Université Rennes 1, 2017. Français. ⟨NNT : 2017REN1S084⟩. ⟨tel-01718135⟩

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