Synthèse en série carbazolique, analogues d'ellipticine, et dihydrocarbazolocarbazoles

Abstract : Ellipticine, a tetracyclic natural alkaloid with the 6H-pyrido[4,3-b]carbazole skeleton and some of its derivatives display antitumoral properties. The aim of this work was firstly to find a general method to synthesize two types of intermediates not described in the literature to our knowledge (carbazole and pyridine derivatives), and then to synthesize some ellipticine analogs, which contain an additional saturated cycle, these structural modifications could be interesting regarding to biological activity. The synthesis was initially thought starting from furan derivatives, and opening of the ring under acidic conditions. 10-Methyl-1,10-dihydrocyclopenta[a]carbazol-3(2H)-one, 1,2,3,11-tetrahydro-4H-benzo[a]carbazol-4-one, 2,3,4,11-tetrahydro-1H-benzo[a]carbazol-1-one, and 11-methyl-1,2,3,11-tetrahydro-4H-benzo[a]carbazol-4-one were eventually obtained by Fischer indole synthesis, followed by Friedel-Crafts reaction for the first product and dissolved metal reduction, DDQ oxidation for the three other molecules. Second hoped intermediates, for instance 5,6,7,8-tetrahydroisoquinoline derivative 3-chloro-7,8-dihydro-6H-isoquinolin-5-one, were not obtained. One of the carbazolic derivatives afforded by the Eloy and Deryckere method ellipticine analogs containing an additional 6-member saturated ring, molecule having a 1,2,3,12-tetrahydroisoquino[5,4-ab]carbazole scaffold. Final product of this synthesis has a polyaminated chain, needed to find a biological activity. Other heterocyclic systems were synthesized from the carbazolic intermediates, like some new dihydrocarbazolocarbazoles
Mots-clés : Ellipticine Carbazole
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Fabien Dufour. Synthèse en série carbazolique, analogues d'ellipticine, et dihydrocarbazolocarbazoles. Autre. Université Paul Verlaine - Metz, 2007. Français. ⟨NNT : 2007METZ031S⟩. ⟨tel-01749024⟩

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