10-Aminomethylene-1,8-dihydroxy-9(10H)-anthracenones: Inhibitory action against 5-lipoxygenase and the growth of HaCaT cells

Article abstract of DOI:10.1016/S0223-5234(97)82775-4

A novel series of 10-aminomethylene substituted 1,8-dihydroxy-9(10H)-anthracenones was synthesized and evaluated both in the bovine polymorphonuclear leukocyte 5-lipoxygenase (5-LO) and in the HaCaT keratinocyte proliferation assay for their enzyme inhibitory and antiproliferative activity, respectively. The synthesis required readily available formanilides as starting materials and a modified Vilsmeier type reaction with the parent anthracenone. The most potent inhibitor of 5-LO was a 4-hydroxyphenyl analog, whereas a 4-nitrophenyl substituent was essential for potent antiproliferative activity. The results of this study indicate that an activated double bond at C-10 of phenylalkylidene-substituted anthracenones is required for potency.