Synthesis, characterization, theoretical, anti-bacterial and molecular docking studies of quinoline based chalcones as a DNA gyrase inhibitor

• A series of quinoline based chalcones A1–A14 were synthesized.
• Their anti-bacterial activity by using method of Minimum Inhibitory Concentration (MIC). Activities were evaluated.
• Tested compounds displayed potential anti-bacterial activity against all bacterial strain.
• Docking studies of chalcones A1–A14 with DNA gyrase were performed.
• Better binding affinities were achieved with novel inhibitors than commercial ones.

A series of fourteen (A1–A14) new qunioline based chalcones were synthesized by condensing 2,7-dichloro-8-methyl-3-formyl quinoline with acetophenone and acetylthiophenes, and subsequently characterized by IR, NMR and Mass spectroscopy. All the compounds were screened for antibacterial activities and found potentially active antibacterial agents. Bioassay, theoretical and dockings studies with DNA gyrase (the enzyme required for super coiling of DNA of bacteria) results showed that the type and positions of the substituents seemed to be critical for their antibacterial activities. The bromo and chloro substituted chalcone displayed high anti-bacterial activity. The A4 and A6 showed high interaction with DNA gyrase, contributing high free binding energy (ΔG −8.18 and −8.88 kcal).

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