Synthesis of prenyloxy coumarin analogues and evaluation of their antioxidant, lipoxygenase (LOX) inhibitory and cytotoxic activity

Umbelliferone, 4-methyl-umbelliferone and their farnesyloxy and geranyloxy analogues were synthesized and evaluated for their antioxidant and soybean lipoxygenase inhibitory activity as well as their cytotoxicity against human neuroblastoma cell line SK-N-SH and human hepatoma cell line HepG2. Auraptene (3), followed by 4-methyl-auraptene (4) exhibit modest cytotoxity against the HepG2 cell line. The novel coumarin 6 combines a satisfactory lipoxygenase inhibitory activity with potent cytotoxicity against SK-N-SH cells, but not against HepG2 cells, thus it could be considered as a lead compound for the development of novel therapeutic agents against neuroblastoma.