Synthesis of a new class of naphthoquinone glycoconjugates and evaluation of their potential as antitumoral agentsElectronic supplementary information (ESI) available. CCDC 1055524 and 1055525. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5ra19192k

A novel series of carbohydrate-based naphthoquinones was synthesized and evaluated for cytotoxicity against different cancer cell lines. The compounds derived from 5-hydroxy-1,4-naphthoquinone (juglone) showed better cytotoxicity profiles against HCT-116, A-549 and MDA-MB 435 human cancer cells than the parent compound. The results suggest that the hydroxyl group on the aromatic ring increased the pro-oxidant activity of these new naphthoquinone derivatives. Furthermore, two derivatives were found to be more active against melanoma cells (MDA-MB435) than the clinically useful anticancer agent doxorubicin, and none of the compounds caused mouse erythrocyte lysis. A novel series of carbohydrate-based naphthoquinones was synthesized and evaluated for cytotoxicity against different human cancer cell lines (HCT-116, A-549 and MDA-MB 435). The compounds derived from juglone showed better cytotoxicity profiles.