Curcumin has been implicated as beneficial in numerous medicinal applications. These include inhibition of tumor propagation, protection against Alzheimer disease and anti-inflammatory properties. It has been found that the modification of the central �-diketone moiety of curcumin to mono-keto group leads to C5-curcuminoids with greater stability, low toxicity and enhanced cancer inhibitory activity. Based on these observations, in the present investigation we have synthesized 18 new symmetrical C5-curcuminoids for evaluating their anticancer. The synthesis was achieved by nucleophilic of the NH group of 4-piperidone hydrochloride, followed by Claisen-Schmidt condensation of the intermediate with a variety of halo substituted benzaldehydes to obtain the desired target molecules. A set of the curcuminoids were tested for anti-cancer activity on 60 human cancer cell lines, which represent diverse histologies. The screening showed some of the compounds to be highly active against different cancer types, causing growth inhibition at nano-molar dose. A mechanistic study using COLO205 cells showed these compounds to cause apoptosis. The Annexin V, DNA Fragmentation, Cell Cycle Effects and Mitochondrial Membrane Permeabilizationtests provide further insight into the mechansim.

Synthesis and anticancer activity of C<sub>5</sub>-curcuminoids

246th National Meeting (2013)

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Synthesis and anticancer activity of C5-curcuminoids

Synthesis and anticancer activity of C₅-curcuminoids