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Wednesday, April 26 • 11:50am - 12:10pm
Combretastatin A-4 Analog Bearing Indole-Chalcone Moiety

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Drugs that target tubulin polymerization have largely been focused on in the field of cancer research. Combretastatin A-4 (CA-4) binds to the colchicine site of ß-tubulin, inhibiting polymerization and thus inducing the subsequent anti-cancer effects. Structural modifications of CA-4 have been made as an attempt to increase the solubility and binding affinity of the compound to the colchicine site. CA-4 analogs that possess indole and chalcone moiety have demonstrated improved anti-cancer effects when compared to the unmodified CA-4 lead compound. This research focuses on synthesizing an analog of CA-4 that incorporates indole-chalcone functional groups, and assessing the efficacy of various reactions in the target molecule synthetic scheme. One of the halogenated acetophenones, α-bromo-3,4,5-trimethoxy acetophenone, has been synthesized and purified via column chromatography. The first step of the indole synthesis was completed, in which a protecting group was added to the hydroxyl of the substituted benzaldehyde starting material. Synthesis of ethyl azidoacetate, the second step of the indole synthesis, has been attempted in two trials. The ethyl azidoacetate product needs to be purified, so that it can be reacted with the protected benzaldehyde to yield the vinyl azide product. The vinyl azide reaction has been attempted using ethyl azidoacetate synthesized by a previous research student, and the two trials were completed using different reagents. Completing the indole synthesis and reacting the substituted indole product with the brominated acetophenone will allow formation of the CA-4 chalcone target molecule through an aldol-condensation reaction.


Wednesday April 26, 2017 11:50am - 12:10pm PDT
123 Zeis Hall