Concise Synthesis and Biological Testing of Natural Products with Potential Anticancer Activity

Natural products are organic compounds that are generated by living organisms as secondary metabolites and may function as defense chemicals. A wide range of natural products have been identified to have significant inhibitory activity vs. certain enzymes. Our products of interest are derivatives of quinones. Modified quinones are a group of molecules found naturally in plants and often exhibit a wide array of biological activities including inhibitory response linked to cancer cell death. However, as they are only generated by organisms in very small amount, the extraction of the molecules from a natural source for biological assays is infeasible. Thus, the research question I hope to answer is how to design and execute novel and innovative synthetic methodologies to produce quinone derivatives in sufficient quantities to test their anticancer activities.

So far, we have been able to successfully develop five different reaction schemes from the literature to synthesize target molecules. We performed the first time ever laboratory synthesis of prenylated quinones found in the leaves and stem of gunnera perpensa and the leaves of pyrola media, respectively. These compounds have been tested recently and showed very promising inhibitory activity. Building on this, we will introduce different side-chains onto 2-methyl-1,4-benzoquinone to investigate unique reaction pathways and their effects on the inhibitory response from molecules synthesized.