Intramolecular Aryne-Furan Cycloadditions for the Synthesis of Anticancer Naphthalimides

Sébastien Prevost 1, 2 Ambre Dezaire 3 Alexandre Escargueil 3
1 DCSO - Laboratoire de synthèse organique
2 MCAM - Molécules de Communication et Adaptation des Micro-organismes (MCAM)
3 CR Saint-Antoine - Centre de Recherche Saint-Antoine
Abstract : An intramolecular aryne Diels-Alder reaction with a furan moiety was applied to the synthesis of dihydrobenzo[ de]isochromenes as intermediates toward naphthalimides. After oxidation, this method offers an efficient approach for the synthesis of substituted naphthalimides, which showed potent cytotoxic activity against HT-29 human cancer cell line.
Keywords : Antineoplastic Agents/chemical synthesis Antineoplastic Agents/chemistry Benzene Derivatives/chemistry Cycloaddition Reaction Furans/chemistry Naphthalimides/chemical synthesis Naphthalimides/chemistry
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Journal articles
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https://hal-polytechnique.archives-ouvertes.fr/hal-02091716
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Submitted on : Saturday, April 6, 2019 - 11:15:17 AM
Last modification on : Friday, April 12, 2019 - 1:31:50 AM

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Sébastien Prevost, Ambre Dezaire, Alexandre Escargueil. Intramolecular Aryne-Furan Cycloadditions for the Synthesis of Anticancer Naphthalimides. Journal of Organic Chemistry, American Chemical Society, 2018, 83 (8), pp.4871-4881. ⟨10.1021/acs.joc.8b00531⟩. ⟨hal-02091716⟩

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