Design and synthesis of novel triple action no-containing monocyclic beta-lactams

Drug resistance in bacteria is a global problem of epic proportions. Drug resistance within tuberculosis is a tremendous issue that especially needs to be addressed. It is extremely important that new antimicrobial agents are developed to help combat this problem. This work described the design and synthesis of novel nitric oxide containing monocyclic beta-lactams that can serve as triple action inhibitors. These triple action inhibitors are designed to inhibit beta-lactamases, Human Leukocyte Elastase, and other serine enzymes. In addition to inhibiting these enzymes, they are designed to release a toxin, nitric oxide, upon binding to the target enzyme. Thus, a resistance enzyme can now become a target for attack and poison release. The synthetic route to the NO containing beta-lactam was successfully accomplished and further studies including biological activity and enzyme binding studies will be performed. The final compound involved a multi-step synthetic route and each compound was characterized by 1H NMR, 13C NMR, and FTIR spectroscopy.