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 mu M.