Leslie Duroure

Natural Product Chemistry Institute, Lutetia Parisorum, Île-de-France, France

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Publications (1)3.57 Total impact

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    ABSTRACT: Simple models of the spiroimine core of (-)-gymnodimine A have been synthesized in racemic and optically active forms. The quaternary carbon of the racemic spiroimines was created by Michael addition of a β-ketoester to acrolein, whereas the asymmetric allylic alkylation of the same β-ketoester was used to access the spiroimines in an enantioselective fashion. Both racemic and enantio-enriched mixtures were tested for their biological activities on Xenopus oocytes either expressing (human α4β2) or having incorporated (Torpedoα1(2)βγδ) nicotinic acetylcholine receptors (nAChRs). These spiroimine analogs of (-)-gymnodimine A inhibited acetylcholine-evoked nicotinic currents, but were less active than the phycotoxin. Our results reveal that the 6,6-spiroimine moiety is important for the blockade of nAChRs and support the hypothesis that it is one of the pharmacophores of this group of toxins.
    Organic & Biomolecular Chemistry 12/2011; 9(23):8112-8. · 3.57 Impact Factor

Publication Stats

3 Citations
79 Views
3.57 Total Impact Points

Institutions

  • 2011
    • Natural Product Chemistry Institute
      Lutetia Parisorum, Île-de-France, France