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A sequence of novel 2-(4-benzoyl-2-methyl-phenoxy)-N-(3-chloro-2-oxo-4-phenyl-azetidin-1-yl)-acetamide analogues <b>9(a–n)</b> were synthesized by multistep synthesis. The newly synthesized compounds were well characterized, and their antimicrobial activities were carried out by disc diffusion and broth dilution methods. Further, all the novel series of compounds (<b>9a</b>–<b>n</b>), were tested against a variety of bacterial and fungal strains in comparison to <i>Ketoconazole, Chloramphenicol,</i> and <i>Amoxicillin</i> as standard drugs, respectively. Compounds <b>9a</b>, <b>9e</b>, and <b>9g</b> as a lead molecule demonstrated a good inhibition against tested strains. Further, molecular docking studies have been performed for the potent compounds to check the three-dimensional geometrical view of the ligand binding to the targeted proteins.