Synthesis of carbohydrate-based naphthoquinones and their substituted phenylhydrazono derivatives as anticancer agents

A novel series of carbohydrate-based 1,2-naphthoquinones 13a-c and their substituted phenylhydrazono derivatives 14a-l were synthesized and evaluated for cytotoxicity against HL-60, MDA-MB435, HCT-116 and SF-295 cancer cell lines. The compounds 9a-c showed the best cytotoxicity profile (IC sub(50) below 2 mu M) against HL-60 and MDA-MB 435 human cells, while the hydrazone derivative 14i (IC sub(50) HL-60 1.65 mu M) was selective for leukemia when compared to the reference drug doxorubicin. None of the compounds exhibited lytic effects against mouse erythrocytes. Characterization of all compounds was confirmed by one- and two-dimensional NMR techniques ( super(1)H, super(13)C-APT, COSY- super(1)H super(1)H and HETCOR super(1)J sub(CH)) and by elemental analysis.