Selenopheno[3,2-c]- and [2,3-c]coumarins: Synthesis, cytotoxicity, angiogenesis inhibition, and antioxidant properties

A simple method for the synthesis of substituted selenopheno[2,3-c] and -[3,2-c]coumarins by treatment of the corresponding ethynylcoumarins with in situ prepared selenium(IV) bromide in 1,4-dioxane-water was elaborated. Molecular structures for selected derivatives were confirmed by X-ray diffraction measurements. The cytotoxic activity of novel selenophenocoumarins showed higher activity and lower acute toxicity than sodium selenite on various tumor cell lines as well as an ability for inhibiting matrix metalloproteinases (MMP-1 – MMP-14), angiogenesis on matrigel in vitro and in vivo. The compounds exhibit antioxidant and prooxidant properties.