Antiangiogenic resveratrol analogues by mild m-CPBA aromatic hydroxylation of 3,5-dimethoxystilbenes.
A mild treatment of the resveratrol analogue 3,5,4'-trimethoxystilbene 2 with m-CPBA afforded two hydroxylated methoxystilbenes 5 and 6 by direct aromatic hydroxylation. A similar protocol was applied to other stilbenes bearing a 3,5-dimethoxy moiety, namely tetramethoxystilbenes 7 and 10 to obtain respectively the hydroxylated analogues 8, 9 and 11, 12. The substrate 2 and the new compounds 5, 8 and 11 were evaluated as anti-angiogenic agents and proved significantly active in the range 1-100 microM.
Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 6, 1-95125 Catania, Italy.
Carmela
C
Spatafora
Giuseppina
G
Basini
Laura
L
Baioni
Francesca
F
Grasselli
Alfio
A
Sofia
Corrado
C
Tringali
D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis*; D000818:Animals; D002460:Cell Line; D002723:Chlorobenzoates / Q000737:chemistry*; D042783:Endothelial Cells / Q000187:drug effects; D008958:Models, Molecular; D015394:Molecular Structure; D000077185:Resveratrol; D013267:Stilbenes / Q000737:chemistry* / Q000494:pharmacology; D013552:Swine
D020533:Angiogenesis Inhibitors; D002723:Chlorobenzoates; D013267:Stilbenes; C000433:3-chloroperbenzoic acid; D000077185:Resveratrol