Synthesis of Novel and Known ꞵ-Carboline Derivatives

Students: Candace Simmons, Lucas Wilson

Faculty Mentor: Steven Farmer

Chemistry

College of Science, Technology, and Business

Our research focuses on carbolines and carboline derivatives that are related to the MAO inhibitory compounds found in Syrian Rue, historically used as a plant medicine by Indigenous peoples. MAO inhibitors can be used to treat challenging mental health and degenerative neurological disorders including depression, anxiety, Parkinson’s Disease, and Alzheimer’s Dementia. The natural compounds this research is inspired by are the harmala alkaloids, β-carbolines. Dr. Farmer identified a synthesis pathway named the Pictet-Spengler synthesis that yields tetrahydro-β-carboline compounds through reacting tryptamine and an aldehyde of choice with trifluoroacetic acid under reflux for 24 hours. This tetrahydro-β-carboline is then refluxed with a catalyst, Palladium (II) on Carbon, in xylene or toluene for a 24-hour period. The crude product of both steps is purified using column chromatography monitored by thin layer chromatography. The final product, after column chromatographic purification, is then recrystallized, yielding an extremely pure final product for analysis using NMR. Our research team was able to synthesize one novel compound and five known compounds over the past year.