Publication Date
2021
Document Type
Thesis
Committee Members
Daniel Ketcha, Ph.D. (Advisor); Patrick Sonner, Ph.D. (Committee Member); Ioana Pavel, Ph.D. (Committee Member)
Degree Name
Master of Science (MS)
Abstract
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.
Page Count
151
Department or Program
Department of Neuroscience, Cell Biology, and Physiology
Year Degree Awarded
2021
Copyright
Copyright 2021, all rights reserved. My ETD will be available under the "Fair Use" terms of copyright law.
