10-Benzoyl-1,8-dihydroxy-9(10H)-anthracenones: Synthesis and biological properties

The synthesis and biological properties of 10-benzoyl-1,8-dihydroxy-9(10H)-anthracenones are described. The compounds were evaluated for their ability to inhibit the growth of the human keratinocyte cell line HaCaT and the 5-lipoxygenase enzyme in bovine polymorphonuclear leukocytes. In addition, generation of hydroxyl radicals was determined as measured by deoxyribose degradation. The results obtained with the new compounds show that substitution with a 4-hydroxy (4f) or a 4-benzyloxy group (4i) at the phenyl ring of the C-10 substituent resulted in potent antiproliferative agents. No correlation was found between hydroxyl-radical formation and the 5-LO inhibitory or antiproliferative action of the compounds.