Studies on quinones. Part 42: Synthesis of furylquinone and hydroquinones with antiproliferative activity against human tumor cell lines

The preparation of furyl-1,4-quinone and hydroquinones by reaction of 2-furaldehyde N,N-dimethylhydrazone with benzo- and naphthoquinones is reported. Access to furylnaphthoquinones from unactivated quinones requires acid-induced conditions, however oxidative coupling reactions of activated quinones proceed under neutral conditions. The in vitro cytotoxic activity of the prepared compounds against a panel of three human cancer cell lines has been studied. Most of the furyl-1,4-quinones exhibited good antiproliferative activity (GI50 = 6.5–33.5 μm) against the MCF-7, NCI-H460, and SF-268 (CNS cancer) cell lines chosen for testing.

Furfural dimethylhydrazone reacts with naphtho- and benzoquinones to give furyl-1,4-naphthoquinones 5, 9, and furyl-1,4-benzoquinones 7, 11, 14, 16. The in vitro evaluation of furylquinone and hydroquinones against a panel of three human tumor cell lines is reported.Figure optionsDownload as PowerPoint slide