Synthesis of cytotoxic ferrocenyl flavones via a ferricenium-mediated 1,6-oxidative cyclization.

ABSTRACT

The oxidation of the ferrocenyl group of 2'-hydroxyferrocenyl chalcones activates the beta-position of the unsaturated ketone to nucleophilic attack to yield the first examples of ferrocenyl flavones. These compounds are significantly more cytotoxic than their organic analogs on B16 melanoma cells, with IC(50) values in the low micromolar range.