Abstract
Combretastatin A-4 (CA-4) has been shown to have anticancer properties by preventing mitosis. However, the active cis-conformation of these molecules are thermodynamically unstable, making it difficult to maintain their activity. Additionally, water solubility and non-specific binding create a need for alternatives to CA-4 drugs. Indole analogs of CA-4 that contain triazoles can be synthesized as a way to create cis-restricted molecules with similar anticancer properties. The triazole takes the place of the cis-alkene and restricts the analog to the cis-conformation. In this experiment, the preparation of vinyl azides will be done via condensation reactions of trimethoxybenzaldehyde and azidoesters, followed by treating them with xylenes to form indoles. The molecules will then be homologenized to create ethynyl indoles and reacted with benzyl azide to form triazoles. The biological activity of these synthesized molecules will be measured and compared to others in the literature to determine their effectiveness. To date, ethylazidoacetate was synthesized from ethylbromoacetate. Several reactions to form vinyl azide were attempted with varying unsuccessful results.
How to Cite
Goudreau, H., (2020) “Synthesis of Triazoles as Combretastatin A-4 Analogs”, Capstone, The UNC Asheville Journal of Undergraduate Scholarship 33(1).
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