Studies on quinones. Part 43: Synthesis and cytotoxic evaluation of polyoxyethylene-containing 1,4-naphthoquinones

A series of naphthoquinones 2,3-disubstituted with chlorine and oxyethylene groups have been prepared from 2,3-dichloro- and 2,3-dimethoxy-1,4-naphthoquinone. The members of these series were tested on normal human fibroblasts and on a panel of four human cancer cell lines. Antitumor activities, which were in the range of IC50 1.3–89.5 μM, discussed in terms of LUMO energy, lipophilicity and size of the polyoxyethylene moiety.

Graphical abstractNaphthoquinones 2,3-disubstituted with chlorine and oxyethylene groups (5, 7–9) were prepared from 2,3-dichloro- and 2,3-dimethoxy-1,4-naphthoquinone. These compounds were tested on normal human fibroblasts and on a panel of four human cancer cell lines. Antitumor activities, which were in the range of IC50 1.3–89.5 μM, are discussed in terms of LUMO energy, lipophilicity, and size of the polyoxyethylene moiety.Figure optionsDownload full-size imageDownload as PowerPoint slide