Multiple Myeloma (MM) is a disorder of differentiated B cells in which the inhibition of the proteasome is standard care. The current drug, bortezomib, used to treat MM is ineffective against drug tolerance where 97% of all patients become intolerant within a few years. Imidazoline scaffolds are capable of overcoming that resistance and delaying MM tumor growth. We believe we will be able to effectively yield imidazolines. Synthesis will occur with commercially available starting materials, making the process less expensive. The process involves 4 steps. While working under inert conditions, we took an acyl chloride, a highly reactive starting material, to make a desired amide. This amide was then transformed to the N-hydroxy amidine. Next, we reacted the hydroxy group on the amidine with an acyl chloride to install a good leaving group on the oxygen. Finally, a combination of secondary amine and α, β unsaturated aldehyde will invoke an iminium that will undergo a Michael Addition. This results in an aziridine that undergoes ring expansion to produce an imidazoline. Using IR analysis, melting point analysis, and nuclear magnetic resonance (NMR) of the products, we concluded that steps one and two yielded the desired compounds. The NMR for step 3 shows our product is present but requires purification to move on to the final step. Using column chromatography, we will separate the compounds based on UV absorption to isolate our purified product. That product will then be carried to step four. Steps 1 through 3 have worked and the outcome of step 4 will allow us to determine the success of our overall project.

Development of new methodology towards accessing 2-imidazoline scaffolds for combatting tuberculosis and multiple myeloma by proteasome modulation

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.