10.1016/j.molstruc.2020.128560
The research focuses on the synthesis, structural characterization, and biological evaluation of a series of brominated plastoquinone analogs (BrPQ1-13). Two different synthetic routes were employed: dibromination followed by oxidation and amination, and oxidation followed by amination and bromination. It was dibrominated and then oxidized to form the corresponding dibrominated 1,4-benzoquinones. Dimethyl hydroquinone was the starting material for the synthesis of the brominated plastoquinone analogs. N-bromosuccinimide (NBS) was employed as a brominating agent in the second synthetic route to brominate the aminoquinones (AQs) that were previously synthesized. The structures of the analogs were determined using spectral data from FTIR, 1H NMR, 13C NMR, and HRMS, with single-crystal X-ray structural characterization for two analogs (BrPQ2 and BrPQ3). The synthesized compounds were evaluated for their in vitro antibacterial and antifungal activities against a panel of ATCC? strains, including seven bacterial strains (three Gram-positive and four Gram-negative) and three fungi, using the broth microdilution method. The study revealed that the presence of an electron-withdrawing group, particularly the trifluoromethyl group, on the phenyl ring positively impacted antibacterial activity, suggesting potential for the development of new antibacterial agents against S. aureus and S. epidermidis.
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