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This coupling reaction of two redox structural motifs, such as 2\u2010bromo\u20101,4\u2010naphthoquinone with diaryldiselenide\/ebselen has been achieved by using sodium borohydride reducing agent at room temperature. Using this approach, several 2\u2010selenylated\u20101,4\u2010naphthoquinones were obtained in moderate to good yields and thoroughly characterized by multinuclear (\n                    <jats:sup>1<\/jats:sup>\n                    H,\n                    <jats:sup>13<\/jats:sup>\n                    C, and\n                    <jats:sup>77<\/jats:sup>\n                    Se) NMR, cyclic voltammetry, and mass spectrometry. Further, light\u2010irradiated thiolation of the synthesized selenazinone was also performed to show the utility of the synthesized compound for post\u2010functionalization. Several 2\u2010selenylated\u20101,4\u2010naphthoquinones were studied by SC\u2010XRD in which intramolecular Se\u22c5\u22c5\u22c5N (from quinolinyl ligand) non\u2010bonded interactions were observed. Photophysical studies (UV\u2010visible, emission, solvatochromism, and quantum yield) were also performed on selected\n                    <jats:italic>C<\/jats:italic>\n                    <jats:sub>2<\/jats:sub>\n                    \u2010selenylated naphthoquinones. The naphthoquinonyl organoseleniums were also screened for their antibacterial properties and quinonyl organoselenium\n                    <jats:bold>5\u2009d<\/jats:bold>\n                    shows good antibacterial potential against\n                    <jats:italic>S. aureus<\/jats:italic>\n                    ATCC 29213 with MIC 0.5\u2005\u03bcg\/mL and a Selectivity Index of &gt;200. Moreover, it also exhibited equipotent activity against various strains of\n                    <jats:italic>S. aureus<\/jats:italic>\n                    and\n                    <jats:italic>Enterococcus faecium<\/jats:italic>\n                    , including strains resistant to vancomycin and meropenem. From structure\u2010activity correlation, it seems that nice blend of oxidant properties from quinone and antioxidant properties from selenium moiety makes it better candidate for antibacterial activity.\n                  <\/jats:p>","DOI":"10.1002\/asia.202401054","type":"journal-article","created":{"date-parts":[[2024,12,24]],"date-time":"2024-12-24T05:49:05Z","timestamp":1735019345000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Design, Synthesis, and Antibacterial Activities of Multi\u2010Functional C\n                    <sub>2<\/sub>\n                    \u2010Functionalized 1,4\u2010Naphthoquinonyl Organoseleniums"],"prefix":"10.1002","volume":"20","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2143-0937","authenticated-orcid":false,"given":"Raushan Kumar","family":"Jha","sequence":"first","affiliation":[{"name":"Department of Chemistry Indian Institute of Science Education and Research Bhopal  Bhopal By-pass Road, Bhauri Bhopal Madhya Pradesh 462066 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0005-1221-4465","authenticated-orcid":false,"family":"Chhavi","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Science Education and Research Bhopal  Bhopal By-pass Road, Bhauri Bhopal Madhya Pradesh 462066 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5193-7026","authenticated-orcid":false,"given":"Svastik","family":"Jaiswal","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Science Education and Research Bhopal  Bhopal By-pass Road, Bhauri Bhopal Madhya Pradesh 462066 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8826-7540","authenticated-orcid":false,"given":"Devendra","family":"Parganiha","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Science Education and Research Bhopal  Bhopal By-pass Road, Bhauri Bhopal Madhya Pradesh 462066 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0003-7862-5334","authenticated-orcid":false,"given":"Vishal","family":"Choudhary","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Science Education and Research Bhopal  Bhopal By-pass Road, Bhauri Bhopal Madhya Pradesh 462066 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9785-6224","authenticated-orcid":false,"given":"Deepanshi","family":"Saxena","sequence":"additional","affiliation":[{"name":"Department of Molecular Microbiology and Immunology CSIR-Central Drug Research Institute  Sitapur Road, Jankipuram Extension Lucknow Uttar Pradesh 226031 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2674-0694","authenticated-orcid":false,"given":"Rahul","family":"Maitra","sequence":"additional","affiliation":[{"name":"Department of Molecular Microbiology and Immunology CSIR-Central Drug Research Institute  Sitapur Road, Jankipuram Extension Lucknow Uttar Pradesh 226031 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0001-4088-5718","authenticated-orcid":false,"given":"Swechcha","family":"Singh","sequence":"additional","affiliation":[{"name":"Department of Molecular Microbiology and Immunology CSIR-Central Drug Research Institute  Sitapur Road, Jankipuram Extension Lucknow Uttar Pradesh 226031 India"},{"name":"AcSIR: Academy of Scientific and Innovative Research (AcSIR)  Ghaziabad Uttar Pradesh 201002 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8823-6074","authenticated-orcid":false,"given":"Sidharth","family":"Chopra","sequence":"additional","affiliation":[{"name":"Department of Molecular Microbiology and Immunology CSIR-Central Drug Research Institute  Sitapur Road, Jankipuram Extension Lucknow Uttar Pradesh 226031 India"},{"name":"AcSIR: Academy of Scientific and Innovative Research (AcSIR)  Ghaziabad Uttar Pradesh 201002 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0658-8709","authenticated-orcid":false,"given":"Sangit","family":"Kumar","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Science Education and Research Bhopal  Bhopal By-pass Road, Bhauri Bhopal Madhya Pradesh 462066 India"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,1,10]]},"reference":[{"key":"e_1_2_9_1_1","unstructured":"\u00a0"},{"key":"e_1_2_9_2_2","doi-asserted-by":"crossref","unstructured":"R.\u2005H. 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