Faculty Sponsor
Dr Eike Bauer
Final Abstract for URS Program
Substituted indoles have significant pharmaceutical relevance and are common building blocks in medicinal chemistry. They are part of many approved drugs across various areas and are also widely explored as leads for antiviral and antibacterial activity. This includes treatment of MRSA, a bacterium type that is resistant to common antibiotics and responsible for complicated infections. Many reactions in pharmaceutical production are slow and inefficient; catalysis facilitates the synthesis of pharmaceutically relevant products. Catalysis provides an efficient, lower-energy pathway to form a product, thereby saving time and energy. Ferrocenium tetrafluoroborate (FcBF4), is a catalyst we are currently investigating. FcBF4 is an iron-based catalyst used in small amounts. Iron is affordable, abundant in the US, and exhibits low toxicity. This is consistent with green-chemistry principles, which are aimed at safer and more affordable ways to synthesize material. It also makes the domestic pharmaceutical industry less dependent on foreign metal sources typically used in pharmaceutical production.
Described in the poster is the application of FcBF4 as a catalyst in a reaction between 2-methylindole and a propargylic alcohol, yielding a substituted 2-methylindole product. The reaction provides a useful synthetic intermediate for pharmaceutical production and allows for testing a diverse library of structural analogs as potential drug candidates. The products of the test reactions are useful for exploring structure-activity relationships, because the molecular structure can be readily transformed into multiple derivatives. Certain indole-containing drugs, such as sumatriptan are used for the acute treatment of migraines. Additional applications of indole-containing compounds include cardiovascular medications treating hypertension such as pindolol. Overall, this work will demonstrate an efficient, low-waste, catalytic route to a variety of substituted indole intermediates that can be diversified for medicinal-chemistry screening.
Presentation Type
Visual Presentation
Document Type
Article