Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB

Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-κB (NF-κB) inhibitor that inhibits DNA binding of NF-κB components including p65. To inspect its biological activity of 1, we synthesized parasitenone (3), possessing the common epoxycyclohexenone moiety of 1. Assessment of the inhibitory activity against NF-κB indicated that the epoxycyclohexenone moiety is the most essential element for the NF-κB inhibitory activity and the salicylic acid moiety may contribute the binding efficiency and specificity.

Graphical abstractParasitenon (2) was synthesized and the inhibitory activity against NF-κB was assessed.Figure optionsDownload full-size imageDownload as PowerPoint slide