Synthesis of nitro-substituted curcumin analogs and their apoptosis-inducing activity on hepatocellular cancer cells / 国际药学研究杂志

ABSTRACT

Objective:To design and synthesize mono-carbonyl curcumin analogs with tumor suppressor activi- ty using substituted benzaldehyde and acetone as the raw material. Methods: Acetone and substituted benzaldehyde were used as starting compounds to synthesize the target compounds via aldol condensation reaction. The antiproliferation activity and apoptosis-inducing activity of target compounds against HepG2 cells were evaluated by MTT assay and flow cytometry, respectively. The medicinal chemical properties of the compounds were calculated online from the website www.molinspiration.com. Results: Six compounds were synthesized and their structures were verified by the 1H NMR, 13C NMR and MS data. Compound 1 exhibited more potent antiproliferative and apoptosis-inducing activity against HepG2 cells than curcumin. The medicinal chemical properties of 1 were more consistent with Lipinski’s Rule of Five and it was ea sier for 1 to penetrate cell membranes than other compounds. Conclusion: The introduction of nitro group into the ortho-position of aromatic rings in mono-carbonyl curcumin analogs could enhance the anticancer activity, which is of great significance for the design and synthesis of mono-carbonyl curcumin analogs with better anticancer activity.