A series of reactions have been explored to modify a moiety within the antibiotic Cefotaxime’s structure to introduce a 1,2,3-triazole into the compound via click chemistry. Triazole containing compounds have come to be recognized for encompassing a broad spectrum of antimicrobial properties and may provide a means of defense against drug- resistant pathogens. This third-generation cephalosporin inhibits cell wall biosynthesis in gram-positive, gram-negative and anaerobic bacteria, however, some strains of bacteria have evolved to code for an enzyme, β-lactamase, that is capable of cleaving the β-lactam ring, thus contributing to the rise of antibiotic resistance. The focus of this project is to develop a synthetic strategy capable of generating dual action antibiotic by the addition of a triazole moiety achieved via the Huisgen 1,3-Dipolar Cycloaddition. Studies towards the synthesis of examples are described, with a goal of testing activity using disk diffusion. Once the synthetic strategy is established, two antibiotic moieties will be linked together, resulting in a dual-action antibiotic.

Synthesis of antibiotic molecules using click chemistry to enhance reactivity

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