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.