The selective force from the ubiquitous use of antibacterial drugs over the past century has pressured bacteria to evolve resistance to their mechanisms of inhibition. This has created a need for the rapid development of new antibacterial drugs that employ novel mechanisms of bacterial inhibition. One such innovation has been the development of oxazolidinone antibacterials. These drugs target the ribosomes of the bacteria and inhibit protein synthesis, leading to cell death. A novel oxazolidinone structure incorporating a benzodioxin ring system has displayed incredible potency against Mycobacterium tuberculosis and other drug-resistant strains of bacteria. This research is aimed at synthesizing a new compound based on this original ring system that incorporates other functional groups into its structure with the hopes of increasing its effectiveness as an antibacterial agent. A beta-hydroxyamide functional group was added onto one of the rings in order to promote water solubility and hydrogen bonding with the enzyme active site. This molecule was synthesized using a six-step synthesis.. The compound was successfully synthesized and has undergone testing for minimum inhibitory concentration at Johns Hopkins University against several strains of bacteria.

Synthesis of a novel oxazolidinone antimicrobial agent

255th National Meeting (2018)

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