Both the resurgence of tuberculosis (TB) and the persistent threat of bacterial resistance continue to threaten modern healthcare. Thus, the need for new means of combating pathogenic bacterial infections is needed. The β-lactam family continues to be a mainstay in the never ending microbial war, still making up over one-half of the antibiotic market. The syntheses of a series of highly functionalized monocyclic β-lactams and cephalosporins are described. Additionally, anti-TB and <i>in vitro</i> β-lactamase inhibitory activities are presented for select compounds. A number of compounds exhibited significant anti-TB and β-lactamase inhibitory activity, with MIC values in the range of 25 to &lt;0.19 µM against TB, and K<sub>i </sub>values in the range of 25-0.03 µM against purified NDM-1 and VIM-1 lysate metallo β-lactamases. This work suggests that these functionally dense scaffolds may serve as promising leads in developing new anti-TB agents and/or metallo β-lactamase inhibitors.

Syntheses and evaluation of highly functionalized monobactams and cephalosporins as medicinally useful agents

249th National Meeting (2015)

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