Charting the Chemical Reactivity Space of Castagnoli-Cushman-Derived N-Heterocyclic Sulfones


Jorge Garcia

Faculty Mentor(s)

Timothy Beng (Chemistry)


N-heterocyclic sulfones are present in many pharmaceuticals, including antityrpanosomal drug Nifurtimox. There is therefore an increasing demand for methodologies that create N-heterocyclic sulfones. This is all the more necessary since drug-resistance issues continue to persist, and there is a decreasing number of potent compounds isolated from nature that tend to satisfy the demands of high throughput screening. This project has achieved a cheap, site-selective, and orientation-selective protocol for constructing N-heterocyclic sulfones. The novel sp3-enriched compounds have considerable structural diversity. Moreover, the approach is highly modular and afforded highly functionalized N-heterocyclic sulfones bearing synthetically useful functional groups such as alkenes, alkynes, and aldehydes. This library of N-heterocyclic sulfone compounds will undergo structure-activity relationship (SAR) studies via an in-house collaboration with Dr. Dondji, with a focus on neglected tropical diseases.

Keywords: Organic Chemistry, Pharmaceuticals, Synthesis


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