This project investigated the synthesis of a more bioactive analogue of the compound curcumin, which is naturally found in the spice turmeric. The challenge of this project was to address both the poor stability and the low solubility of the naturally occurring compound. Research has shown that diarylidenylpiperidone (DAP) compounds are viable analogues of curcumin. A diarylidenylpiperidone ring was used to replace the dicarbonyl moiety of curcumin to make the analogue stable at physiological pH. Attachment of poly(ethylene glycol) substituents to the phenolic hydroxyl groups of vanillin, used as a starting material in the synthesis of the DAP analogue, was attempted to increase aqueous solubility. The significance of this project is to enhance the many medicinal properties associated with curcumin, including uptake by cells to selectively induce apoptosis in cancerous cells. Future research might involve other methods of increasing the solubility of DAP compounds and assaying the efficacy of these compounds in cancerous cell lines.

Synthesis, characterization, and analysis of diarylidenylpiperidone analogs of curcumin

249th National Meeting (2015)

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