Intramolecular Aryne-Furan Cycloadditions for the Synthesis of Anticancer Naphthalimides

Sébastien Prevost; Ambre Dezaire; Alexandre Escargueil

doi:10.1021/acs.joc.8b00531

Journal articles

Intramolecular Aryne-Furan Cycloadditions for the Synthesis of Anticancer Naphthalimides

Sébastien Prevost ^{1, 2, 3} Ambre Dezaire ⁴ Alexandre Escargueil ⁴

1 DCSO - Laboratoire de synthèse organique

2 MCAM - Molécules de Communication et Adaptation des Micro-organismes

3 Laboratoire Charles Friedel

4 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 : Furans/chemistry Naphthalimides/chemical synthesis Naphthalimides/chemistry Cycloaddition Reaction Benzene Derivatives/chemistry Antineoplastic Agents/chemistry Antineoplastic Agents/chemical synthesis

Document type :

Journal articles

Domain :

Chemical Sciences / Organic chemistry

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https://hal-polytechnique.archives-ouvertes.fr/hal-02091716
Contributor : Aurélien Arnoux <>
Submitted on : Saturday, April 6, 2019 - 11:15:17 AM
Last modification on : Tuesday, September 22, 2020 - 3:38:43 AM

Intramolecular Aryne-Furan Cycloadditions for the Synthesis of Anticancer Naphthalimides

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Intramolecular Aryne-Furan Cycloadditions for the Synthesis of Anticancer Naphthalimides

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