Synthesis of novel 7-oxo and 7-hydroxy trifluoroallocolchicinoids with cytotoxic effect

Elizabeth Chosson (1, 2) , Francesca Santoro (2) , Christophe Rochais (2) , Jana Sopkova-de Oliveira Santos (2) , Rémi Legay (2) , Sylviane Thoret (3) , Thierry Cresteil (3) , Maria Stefania Sinicropi (4) , Thierry Besson (1) , Patrick Dallemagne (2)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 CERMN - Centre d'Etudes et de Recherche sur le Médicament de Normandie
3 ICSN - Institut de Chimie des Substances Naturelles
4 Unical - Università della Calabria [Arcavacata di Rende]

The synthesis of 7-oxo and 7-hydroxy trifluoroallocolchicinoids was achieved through the intramolecular cyclization of o-phenyl-β-phenylalanines. The resulting compounds were evaluated for their cytotoxic activity against KB cells and their inhibitory effect towards the polymerization of tubulin. The results yielded some potent cytotoxic compounds with correlated partial antitubulin effect.

Domains: Chemical Sciences; Organic chemistry; Chemical Sciences; Analytical chemistry; Chemical Sciences; Catalysis; Chemical Sciences; Medicinal Chemistry

Elizabeth Chosson, Francesca Santoro, Christophe Rochais, Jana Sopkova-de Oliveira Santos, Rémi Legay, et al.. Synthesis of novel 7-oxo and 7-hydroxy trifluoroallocolchicinoids with cytotoxic effect. Bioorganic and Medicinal Chemistry Letters, 2012, 20 (8), pp.2614-2623. ⟨10.1016/j.bmc.2012.02.043⟩. ⟨hal-02357753⟩