Design, Synthesis, and Antibacterial Activities of Multi-Functional C2-Functionalized 1,4-Naphthoquinonyl Organoseleniums.

A practical and efficient reaction for C2-selenylation of 1,4-naphthoquinones has been explored. This coupling reaction of two redox structural motifs, such as 2-bromo-1,4-naphthoquinone with diaryldiselenide/ebselen has been achieved by using sodium borohydride reducing agent at room temperature. Using this approach, several 2-selenylated-1,4-naphthoquinones were obtained in moderate to good yields and thoroughly characterized by multinuclear (1H, 13C, and 77Se) NMR, cyclic voltammetry, and mass spectrometry. Further, light-irradiated thiolation of the synthesized selenazinone was also performed to show the utility of the synthesized compound for post-functionalization. Several 2-selenylated-1,4-naphthoquinones were studied by SC-XRD in which intramolecular Se⋅⋅⋅N (from quinolinyl ligand) non-bonded interactions were observed. Photophysical studies (UV-visible, emission, solvatochromism, and quantum yield) were also performed on selected C2-selenylated naphthoquinones. The naphthoquinonyl organoseleniums were also screened for their antibacterial properties and quinonyl organoselenium 5 d shows good antibacterial potential against S. aureus ATCC 29213 with MIC 0.5 μg/mL and a Selectivity Index of >200. Moreover, it also exhibited equipotent activity against various strains of S. aureus and Enterococcus faecium, including strains resistant to vancomycin and meropenem. From structure-activity correlation, it seems that nice blend of oxidant properties from quinone and antioxidant properties from selenium moiety makes it better candidate for antibacterial activity.