Synthesis of novel kavain-like derivatives and evaluation of their cytotoxic activity

Patricia de A. Amaral , Julien Petrignet (1) , Nicolas Gouault (2, 3) , Taciane Agustini , Françoise Lohézic-Le Dévéhat (3) , Alexandre Cariou (3) , René Grée (1) , Vera L. Eifler-Lima , Michèle David (3)

1 CPM - Chimie et Photonique Moléculaires
2 ISCR - Institut des Sciences Chimiques de Rennes
3 Substances Lichéniques et Photoprotection

Palladium-catalyzed cross coupling reactions (Sonogashira-Hagihara, Suzuki-Miyaura, and Heck) coupling and nickel hydride-mediated tandem isomerization aldolisation have been used for the synthesis of three series of δ-valerolactones substituted in positions 3, 4, 5 and 6 of the lactone ring. The 26 kavaïn-like derivatives were tested against three cell lines and five of them exhibited a weak cytotoxic activity.

Domains: Chemical Sciences

Patricia de A. Amaral, Julien Petrignet, Nicolas Gouault, Taciane Agustini, Françoise Lohézic-Le Dévéhat, et al.. Synthesis of novel kavain-like derivatives and evaluation of their cytotoxic activity. Journal of the Brazilian Chemical Society, 2009, 20, pp.1687-1697. ⟨10.1590/S0103-50532009000900018⟩. ⟨hal-01470075⟩