Synthesis, spectral characterization, crystal structure and molecular docking study of 2,7-diaryl-1,4-diazepan-5-ones

• Seven new diazepan-5-ones have been synthesized and characterized using NMR spectra.
• X-ray crystal structures have been solved for compounds 9 and 11.
• Diazepan-5-ones adopt chair conformation in solution and solid states.
• Docking studies confirm the binding of active compounds with MRSA.
• Compounds have been evaluated for their antibacterial and antioxidant activities.

In this study, a series of variously substituted r-2,c-7-diaryl-1,4-diazepan-5-ones 9–16 have been synthesized using Schmidt rearrangement and are characterized by IR, mass and 1D & 2D NMR spectral data. The proton NMR coupling constant and estimated dihedral angles reveal that the compounds 9–16 prefer a chair conformation with equatorial orientation of alkyl and aryl groups. Single crystal X-ray structure has been solved for compounds 9 and 11 which also indicates the preference for distorted chair conformation with equatorial orientation of substituents. The compounds 9–16 have been docked with the structure of Methicillin-resistant Staphylococcus aureus (MRSA) and the results demonstrate that compound 10 is having better docking score and glide energy than others and it is comparable to co-crystal ligand. Furthermore, all the compounds have been evaluated for their antibacterial and antioxidant activities. All the compounds show moderate antibacterial activity and only 11 exhibits better activity against S. aures and Escherichia coli. The compounds 11, 13 and 14 exhibit half of the antioxidant power when compared to the BHT and the remaining compounds show moderate activity.

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