Nouvelle voie de synthèse de systèmes piperazines de type phthalascidine

Abstract : This manuscript describes the synthesis and the biological evaluation of tetrahydroisoquinolines, (1,3')-bis-tetrahydroisoquinolines and polycyclic piperazine systems contained in the ecteinascidin and phthalascidin families.
Firstly, we studied the synthesis of tetrahydroisoquinolines incorporating heterocyclic structures in order to apply this method to the synthesis of (1,3')-bis-tetrahydroisoquinolines as synthetic intermediates of polycyclic piperazine systems. The inhibition of cancer cell proliferation and the mode of action of these compounds were assessed in collaboration with the “Centre for Molecular Drug Design” (University of Salford, United Kingdom) under the supervision of Professor Sylvie Ducki.
Secondly, we considered a new synthetic approach concerning the synthesis of ecteinascidin derivatives through the exploration of the oxidative nucleophilic substitution of benzylic position. This method was developed from a L-DOPA derivative by substitution of benzylic position in presence of the oxidizing agent 1,3-dichloro-5,6-dicyanobenzoquinone.
Finally, with promising biological evaluation results, we realized the synthesis of fully functionalized α-amino-alcool as synthetic precursors for the preparation of phthalascidin analogues from two available commercial compounds in order to assess the biological properties of our compounds
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Submitted on : Tuesday, October 16, 2007 - 2:51:28 PM
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Sylvain Aubry. Nouvelle voie de synthèse de systèmes piperazines de type phthalascidine. Catalyse. Université Claude Bernard - Lyon I, 2007. Français. ⟨tel-00179725⟩

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