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 which employ new 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, effectively causing cell death. A novel oxazolidinone structure incorporating a fused cyclic ring system has displayed incredible potency against <i>Mycobacterium tuberculosis </i>and other drug-resistant strains of bacteria. This research is aimed at synthesizing a new series of compounds based on this fused cyclic ring system that incorporate other functional groups into their structure with the hopes of increasing their effectivity as antibacterial agents. Amide and hydroxyl functional groups were added for their hydrogen bonding capabilities to better bind to the ribosome; a carboxylic acid functional group was added to facilitate entry of the drug into the bloodstream; and the final derivative had one of its oxygen atoms replaced with a nitrogen atom in an attempt to make the molecule more water soluble and potentially cause it to fit better into the ribosome. These molecules were synthesized using an eight step synthesis. More recently, a four step synthesis has been devised to synthesize the oxazolidinone derivatives whose functional groups contain acidic protons.

Synthesis of novel oxazolidinone anitbacterials

253rd National Meeting (2017)

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