The application of anthraquinone-based triazenes as equivalents of diazonium salts in reaction with methylene active compounds

A series of polyfunctionalized anthraquinonehydrazones have been prepared using azo-coupling reaction between anthraquinone-based triazenes and methylene active compounds in acetic acid without a catalyst. The structures of new synthesized compounds were confirmed by their IR, LCMS,¹H and ¹³C NMR spectroscopic data. Some of the synthesized compounds were screened for their in vitro anticancer activity according to US NCI protocols. Biological screening data led to the identification of 1-{N’-[3-(4-hydroxyphenyl)-4-oxo-2-thioxothiazolidin-5-ylidene]hydrazino}anthraquinone 3.4 as having antitumor activity on the non-small cell lung cancer NCI-H460 (GP = 13.25%) and colon cancer HCT-116 (GP = 13.69%) cell lines.