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A series of new Coumarin hydrazone oxime scaffolds were synthesised as potential anti‐TB agents. The structures of the scaffolds were confirmed by spectroscopic and analytical techniques. X‐ray crystallography confirmed the structure of compound 6‐methyl‐4‐((((Z)‐((E)‐3‐(2‐phenylhydrazono)butan‐2‐ylidene)amino)oxy)methyl)‐2H‐chromen‐2‐one (5a). The coumarin hydrazone oxime scaffolds were tested in‐vitro against the Mycobacterium tuberculosis H37Rv strain, and Vero cells were used to assess cytotoxicity. Compound 5b was obtained as the hit candidate, exhibiting MIC 0.78 μg/mL, showing more potent anti‐TB activity than Rifamycin and comparable activity to Isoniazid. There was minimal cytotoxicity observed against Vero cells for the most active compounds, indicating a good safety‐profile.In addition, the most diligent compound 5b demonstrated substantial binding interactions at the PDB:4DQU enzyme's active site and also displayed greater C‐score value than that of 4DQU ligand which validates the observed results. [ABSTRACT FROM AUTHOR]

• A series of new coumarino-azetidinones (3a-l) were designed and synthesized. • All the compounds were screened for antitubercular and antimicrobial activity. • Compounds 3e and 3k emerged out as promising antituberculars and antimicrobials. • Compounds 3e and 3k were exhibited comparatively less toxicity. • Excellent molecular docking scores were observed. In the present work, a series of new coumarino-azetidinones (3a-l) were designed, synthesized and evaluated for biological activities. The newly synthesized compounds (3a-l) were fully characterized by several spectroscopic techniques and elemental analyses. The synthesized compounds (3a-l) were screened for their preliminary in-vitro antitubercular and antimicrobial activities. Almost all the coumarino-azetidinones showed promising activity against Mycobacterium tuberculosis (M. tuberculosis) H 37 Rv strain. Conversely, some of the coumarino-azetidinones displayed interesting antimicrobial activities. Moreover, most active compounds were tested for cytotoxicity studies and exhibited low-level cytotoxicity towards Vero cells. Last but not the least, molecular docking results showed excellent interactions with M. tuberculosis InhA-D148G mutant (PDB. 4TZK) and Escherichia coli (E. coli) (PDB. 4JX8). The results of biological evaluation suggest that the coumarino-azetidinones are promising lead compounds for the subsequent investigation in search of new antitubercular and antimicrobial agents. Image, graphical abstract In the present study, a series of new coumarino-azetidinones were synthesized, characterized and evaluated for their preliminary antitubercular, antimicrobial and cytotoxicity activity. [ABSTRACT FROM AUTHOR]