Every year the number of multidrug resistant bacteria and viruses increases, triggering a tremendous need for the development of more powerful countermeasures. Modification of current medicinal compounds is a short-term solution, but the need for novel medicinal compounds is critical in the greater scheme. The use of boron containing structures as potential antibiotics and antivirals has been investigated, and have shown great potential as therapeutic compounds. The three current boron containing FDA approved medications indicate that there is lots of potential for further discovery and development. Currently, our research group focuses its efforts on boron modified inhibitors of HIV-1 aspartic protease. Boron-modified protease inhibitors have been shown to act as “dual mode” inhibitors. Furthermore, boron’s dynamic coordinate system increases the inhibitor’s affinity for an active site when compared to carbon containing analogues. These special properties of boron are advantageous for more efficient and effective protease inhibition. By creating a library of novel boronates, through homologation followed by nucleophilic bimolecular substitution, synthetic challenges often encountered with boron containing compounds were tested. The tested synthetic pathway began with the synthesis of a α-chloroalkylboronic pinacol ester from benzylboronic pinacol ester. α-Chloroalkylboronic pinacol ester was then combined with a variety of R groups to produce new boronates. Unsurprisingly, the relative bulkiness of the R group was the largest factor affecting product yield. The majority of the boronates proved to be stable on both GC/MS and silica gel.

Discovery of novel boronates: Structural building blocks of potential enzyme inhibitors

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.