Multifaceted Study on a Cytochalasin Scaffold: Lessons on Reactivity, Multidentate Catalysis, and Anticancer Properties

Abstract : We report an intramolecular Diels-Alder reaction efficiently accelerated by Schreiner's thiourea, to build a functionalized cytochalasin scaffold (periconiasin series) amenable to biological purpose. DFT calculation highlighted a unique multidentate cooperative hydrogen bonding in this catalysis. The deprotection end-game afforded a collection of diverse structures and showed the peculiar reactivity of the Diels-Alder cycloadducts upon functionalization. Biological studies revealed strong cytotoxicity of a few compounds on breast cancer cell lines, while preserving actin polymerization.
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Mehdi Zaghouani, Oscar Gayraud, Vincent Jactel, Sébastien Prevost, Ambre Dezaire, et al.. Multifaceted Study on a Cytochalasin Scaffold: Lessons on Reactivity, Multidentate Catalysis, and Anticancer Properties. Chemistry - A European Journal, Wiley-VCH Verlag, 2018, 24 (62), pp.16686-16691. ⟨10.1002/chem.201804023⟩. ⟨hal-02135339⟩

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