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A series of new urea derivatives, containing aryl moieties as potential antimicrobial agents, were designed, synthesized, and characterized by ¹H NMR, ¹³C NMR, FT-IR, and LCMS spectral techniques. All newly synthesized compounds were screened in vitro against five bacterial strains (<i>Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa,</i> and <i>Staphylococcus aureus</i>) and two fungal strains (<i>Candida albicans</i> and <i>Cryptococcus neoformans</i>). Variable levels of interaction were observed for these urea derivatives. However, and of major importance, many of these molecules exhibited promising growth inhibition against <i>Acinetobacter baumannii</i>. In particular, to our delight, the adamantyl urea adduct <b>3l</b> demonstrated outstanding growth inhibition (94.5%) towards <i>Acinetobacter baumannii</i>. In light of this discovery, molecular docking studies were performed in order to elucidate the binding interaction mechanisms of the most active compounds, as reported herein.