Fiche publication


Date publication

juillet 2021

Journal

Bioorganic & medicinal chemistry

Auteurs

Membres identifiés du Cancéropôle Est :
Pr BOURA Cédric


Tous les auteurs :
Ariztia J, Chateau A, Boura C, Didierjean C, Lamandé-Langle S, Pellegrini Moïse N

Résumé

The [3.3.0]furofuranone structure is found in numerous families of biologically active natural products. We took advantage of the stereodiversity afforded by carbohydrate derivatives to prepare several compounds structurally similar to goniofufurone and crassalactones which are natural cytotoxic agents. We designed and synthesized several stereoisomers of these natural compounds via lactonization of C-glycosyl compounds bearing an hydroxyl on position 4 and a methyl ester on the pseudo-anomeric positionThe reactivity of this bicyclic moiety was explored through etherification of hydroxyls in position 5 and 7 and various substituants (halogen, phenyl, benzyl, cynanmoyl) were introduced. The anti-proliferative properties of these mimics were then evaluated on various cancer cell lines and two compounds 24 and 35 demonstrated IC value of 1.34 µM (U251) and 7.60 µM (U87) respectively.

Mots clés

Anti-proliferative compound, C-glycosyl compound, Furofuranone

Référence

Bioorg Med Chem. 2021 Jul 21;45:116313