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University of New Hampshire
Chemistry
2016
Mentor: Dr. Marc Boudreau, Department of Chemistry
Synthesis and evaluation of carbapenem β-lactams containing bulky hydrophobic C-6 side chains as potential inhibitors of carbapenemases
Bacterial resistance against antibiotics is on the rise across the nations. Every antibiotic introduced to the clinic has developed resistance against it, making the discovery of new anti-bacterial medicines one of the top public health priorities. b-Lactam antibiotics are among the most successful antibiotics ever introduced to combat bacterial infections, however the rise of resistance has called for structural modifications in the search for new methods of fighting against infection. This has resulted in the introduction of the carbapenem class of b-lactams (e.g. meropenem, doripenem) into the clinic; however, resistance to this class has emerged as well. Carbapenems are often used to treat infections as a last resort; therefore the increasing resistance against them is particularly distressing. This proposal hypothesizes that by introducing a bulky, hydrophobic, C-6 side chain to a carbapenem, enzymes in the bacteria will not be able to disable the function of the antibiotic. The new compound 2 will be synthesized in multiple steps as shown in Scheme 1.