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All previously reported PDF inhibitors with sufficient antibacterial activity share the structural feature of a 2-substituted alkanoyl at the P<jats:sub>1<\/jats:sub>\u2032 site. Using a combination of iterative parallel synthesis and traditional medicinal chemistry, we have identified a new class of PDF inhibitors with<jats:italic>N<\/jats:italic>-alkyl urea at the P<jats:sub>1<\/jats:sub>\u2032 site. Compounds with MICs of \u22644 \u03bcg\/ml against gram-positive and gram-negative pathogens, including<jats:italic>Staphylococcus<\/jats:italic><jats:italic>aureus<\/jats:italic>,<jats:italic>Streptococcus<\/jats:italic><jats:italic>pneumoniae<\/jats:italic>, and<jats:italic>Haemophilus<\/jats:italic><jats:italic>influenzae<\/jats:italic>, have been identified. The concentrations needed to inhibit 50% of enzyme activity (IC<jats:sub>50<\/jats:sub>s) for<jats:italic>Escherichia<\/jats:italic><jats:italic>coli<\/jats:italic>Ni-PDF were \u22640.1 \u03bcM, demonstrating the specificity of the inhibitors. In addition, these compounds were very selective for PDF, with IC<jats:sub>50<\/jats:sub>s of consistently &gt;200 \u03bcM for matrilysin and other mammalian metalloproteases. Structure-activity relationship analysis identified preferred substitutions resulting in improved potency and decreased cytotoxity. One of the compounds (VRC4307) was cocrystallized with PDF, and the enzyme-inhibitor structure was determined at a resolution of 1.7 A\u030a. This structural information indicated that the urea compounds adopt a binding position similar to that previously determined for succinate hydroxamates. Two compounds, VRC4232 and VRC4307, displayed in vivo efficacy in a mouse protection assay, with 50% protective doses of 30.8 and 17.9 mg\/kg of body weight, respectively. 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