Sulfonamides are important bioisosteres found at the core of a variety of bioactive and pharmaceutical compounds. Sulfonamide-containing compounds have been shown to have a wide range of capabilities, including antiviral, antibacterial, antimalarial, antifungal, anti-inflammatory, and anticancer activities. The mild and direct incorporation of a sulfonamide unit into an aromatic or heteroaromatic core is a valuable pursuit in molecular synthesis. To this end, we have developed a new reaction that directly incorporates an N-sulfonyl unit at sterically hindered alkyl halide locations. During our initial investigation, we observed installation of N-sulfonyl units to polycyclic aromatic hydrocarbon (PAH) scaffolds, such as fluorene. The fluorene scaffold has been observed as a structure found within bioactive molecules, specifically with a substituent attached in the 9-position. Our progress towards the production of halogenated fluorene and heteroanthracene scaffolds, the subsequent installation of N-sulfonyl unit, and the cell viability studies of the synthesized compounds will be presented.

Synthesis of a library of N-sulfonyl analogs of substituted fluorene and dihydroheteroanthracene scaffolds

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.