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This study aimed to synthesize C3\u2010indole derivatives linked to various heterocyclic scaffolds, including thiophenes, thiazolidine\u20104\u2010ones, and 1,3,4\u2010thiadiazoles, <jats:italic>via<\/jats:italic> the reaction of ethylthioacetanilide <jats:bold>2<\/jats:bold> with different \u03b1\u2010haloketones.The structures of the target compounds were established using <jats:sup>1<\/jats:sup>H and <jats:sup>13<\/jats:sup>C nuclear magnetic resonance spectroscopy, mass spectrometry, infrared spectroscopy, and elemental analysis. The synthesized compounds were tested for antimicrobial activity against different microbes: <jats:italic>S. aureus<\/jats:italic> ATCC 6538 (Gram\u2010positive bacteria), <jats:italic>E. coli<\/jats:italic> ATCC 25933 (Gram\u2010negative bacteria), <jats:italic>C. albicans<\/jats:italic> ATCC 10231 (yeast), and fungi (<jats:italic>A. niger<\/jats:italic> NRRL\u2212A326). Thiophene <jats:bold>6a<\/jats:bold>, thiazolidine\u20104\u2010one <jats:bold>8<\/jats:bold>, and compound <jats:bold>10d<\/jats:bold> exhibited the highest antimicrobial activities. The molecular docking study showed that compounds <jats:bold>2<\/jats:bold>, <jats:bold>4<\/jats:bold>, <jats:bold>6a<\/jats:bold>, and <jats:bold>6c<\/jats:bold> had good binding energy and favorable binding modes of interactions with the DNA gyrase B enzymes (PDB: 3\u2005U2D) and (PDB: 1S14). The results showed that the NH group of the indole in compounds <jats:bold>2<\/jats:bold> and <jats:bold>4<\/jats:bold>, together with the nitrile group (CN), played an important role in inhibiting DNA gyrase B of <jats:italic>S. aureus<\/jats:italic>, PDB: 3\u2005U2D. Furthermore, the NH of the indole ring, together with the ethylamino group of compound <jats:bold>2<\/jats:bold>, was crucial in inhibiting DNA gyrase B of <jats:italic>E. coli<\/jats:italic>, PDB: 1S14. These findings may encourage researchers to develop more effective C3\u2010indole derivatives in their search for antimicrobial drugs.<\/jats:p>","DOI":"10.1002\/cbdv.202402325","type":"journal-article","created":{"date-parts":[[2024,10,22]],"date-time":"2024-10-22T02:32:37Z","timestamp":1729564357000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Synthesis, Biological Evaluation, and Molecular Docking Studies of Indole\u2010Based Heterocyclic Scaffolds as Potential Antibacterial Agents"],"prefix":"10.1002","volume":"22","author":[{"given":"Hemat S.","family":"Khalaf","sequence":"first","affiliation":[{"name":"Department of Photochemistry National Research Centre, Dokki  Cairo 12622 Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mohamed S.","family":"Abdel\u2010Aziz","sequence":"additional","affiliation":[{"name":"Microbial Chemistry Department Biotechnology Research Institute, National Research Centre, Dokki  Giza Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2151-6802","authenticated-orcid":false,"given":"Mohamed. 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