According to statistical data from the Department of Health of Puerto Rico and United States, cancer is the second cause of death, making it one of the most life threatening diseases of this time. The current chemotherapy treatments are both highly expensive and toxic, which creates a critical need to discover more effective and less toxic anticancer drugs. Curcumin is a natural compound that has biological properties such as anti-cancer, anti-Alzheimer, and anti-microbial. Although curcumin is an attractive lead compound due to it easy synthesis, several disadvantages such as poor bioavailability, fast metabolism and the requirement of repetitive doses, have been attributed this compound. Our research group is addressing the problem above by synthesizing novel C5-curcumin-fatty acid (C5-curc-FA) conjugates, which have the potential of being anticancer drugs. We have preliminary data that supports that the conjugation of fatty acid group to C5-curcumin will improve its anticancer properties. The synthetic approach used on this project involves a two-step synthesis. The first step consisted in a Steglich type reaction, where a phenolic aldehyde was reacted with a desired fatty acid. The resulting acyl-protected phenolic aldehydes were subsequently reacted with either acetone or cyclohexanone through an Aldol condensation to yield the desired C5-curc-FA conjugates.The newly synthesized C5-curc-FA conjugates are expected to display good cytotoxicity towards normal human cells and potent anticancer properties against different cancer cell lines.

Total synthesis of novel analogs of C-5 curcumin fatty acid conjugates and their potential as anticancer compounds

247th National Meeting (2014)

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