Synthesis of anti-proliferative [3.3.0]furofuranone derivatives by lactonization and functionalization of C-glycosyl compounds - Université de Lorraine Accéder directement au contenu
Article Dans Une Revue Bioorganic and Medicinal Chemistry Letters Année : 2021

Synthesis of anti-proliferative [3.3.0]furofuranone derivatives by lactonization and functionalization of C-glycosyl compounds

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 IC50 value of 1.34 µM (U251) and 7.60 µM (U87) respectively

Domaines

Chimie
Fichier principal
Vignette du fichier
manuscrit for Hal.pdf (701.18 Ko) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)

Dates et versions

hal-03356372 , version 1 (28-09-2021)

Licence

Paternité - Pas d'utilisation commerciale - Pas de modification

Identifiants

Citer

Julen Ariztia, Alicia Chateau, Cédric Boura, Claude Didierjean, Sandrine Lamandé-Langle, et al.. Synthesis of anti-proliferative [3.3.0]furofuranone derivatives by lactonization and functionalization of C-glycosyl compounds. Bioorganic and Medicinal Chemistry Letters, 2021, 45, pp.116313. ⟨10.1016/j.bmc.2021.116313⟩. ⟨hal-03356372⟩
62 Consultations
86 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More