Daniel Ketcha, Ph.D. (Advisor); Patrick Sonner, Ph.D. (Committee Member); Ioana Pavel, Ph.D. (Committee Member)
Master of Science (MS)
With the intent to create an optimized monoamine oxidase-B (MAO-B) inhibitor, researchers in this investigation synthesized derivatives of the benzylidene oxindole scaffold in order to determine a lead molecule for further drug development. Previous work in this laboratory group evaluated a similar scaffold, the chalcone structural unit. As this class of compounds was determined to possess the ability to permeate the blood brain barrier (BBB) and to act as potent MAO-B inhibitors, it was posited that scaffold hopping from this previously studied molecular skeleton to benzylidene oxindoles would provide analogous results. Benzylidene oxindoles are readily synthesized via the Claisen-Schmidt condensation of an indolin-2-one and a substituted benzaldehyde. Based on this simple synthesis, a large library of compounds has the potential to be made readily, increasing the possibility that a lead molecule may be determined subsequent to biological screening. During the course of this research investigation, a large, although not exhaustive, number of functionalized benzylidene oxindoles was synthesized in order to determine which structural units would improve the scaffold’s ability to act as a reversible MAO-B specific inhibitor. This could then potentially be used in addition to the pro-drug Levadopa in order to ameliorate Parkinson’s disease symptoms.
Department or Program
Department of Neuroscience, Cell Biology, and Physiology
Year Degree Awarded
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