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Multifaceted Study on a Cytochalasin Scaffold: Lessons on Reactivity, Multidentate Catalysis, and Anticancer
Mehdi Zaghouani1, Oscar Gayraud2, Vincent Jactel2
1Muséum National d'Histoire Naturelle, Unité Molécules de Communication et Adaptation des Micro-organismes, CNRS, 57 rue Cuvier, 75005, Paris, France.
Abstract:
An intramolecular Diels-Alder (IMDA) reaction efficiently accelerated by Schreiner's thiourea is reported, to build a functionalized cytochalasin scaffold (periconiasin series) for biological purposes. 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 actin polymerization is preserved.
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