NAD(P)H: Quinone oxidoreductase 1 inducer activity of some enaminone derivatives

The present work reports the synthesis of some enaminone derivatives bearing the biologically active 3,4-dimethoxyphenyl (3) or 3,4,5-trimethoxyphenyl moieties (5 and 7), respectively. The trimethoxybenzene moiety has been previously reported to confer cytotoxic activity. However, we found that, at high micromolar concentrations, the new compounds have the ability to weakly induce the cytoprotective enzyme NQO1. This is most likely due to their electrophilic cyclohexenone functionality, a well-established structural feature of NQO1 inducers. The structure of the newly synthesized compounds was confirmed on the basis of elemental analyses, IR,¹HNMR,¹³C-NMR spectra.