Synthesis and computational investigation of N,N-dimethyl-4-[(Z)-(phenylimino)methyl]aniline derivatives: Biological and quantitative structural activity relationship studies

This study describes the synthesis, characterisation and biological activities of four Schiff base compounds, namely: N, N-dimethyl-4-(((4-nitrophenyl)imino)methyl)aniline (ABS1), 4-(((2-chlorophenyl) imino)methyl)-N,N-dimethylaniline (ABS2), 4-bromo-2-chloro-N-(4-dimethylamino)benzylidene) aniline (ABS3), and N,N-dimethyl-4-(((2-(trifluoromethyl)phenyl)imino)methyl)aniline (ABS4). These compounds were characterised by UV-Visible, FTIR, CHN-elemental analysis, PXRD, HRMS, and NMR ( 1 H, 13 C, DEPT, 1 H 1 H- COSY, NOESY, HSQC, and HBMC) spectroscopic techniques. Furthermore, compounds ABS2-4 were suitable for single crystal X-ray diffraction analysis, and support the structures proposed. The antibacte-rial, antifungal and antioxidant activities of the compounds were investigated using both micro dilution and DPPH radical scavenging assays, showing a broad range of activity from high to moderate. Computa-tional chemistry (molecular electrostatic potential maps, conceptual density functional theory calculations and non-covalent-interactions analysis) correlates with the experimental electronic properties as well as structure-reactivity relationship for the drug-likeness properties of the compounds. Molecular docking studies identified potential binding modes of the compounds, and the results corroborate with those ob-tained from MIC and MFC studies. The lead compounds (ABS1 and ABS3) exhibit outstanding drug-like properties.(c) 2022 Elsevier B.V. All rights reserved.

Automated summary

This study reports the synthesis, characterisation, and biological activities of four Schiff base compounds. The compounds were characterised using various spectroscopic techniques and X-ray diffraction analysis. The antibacterial, antifungal, and antioxidant activities of the compounds were evaluated, showing a wide range of activities. Computational chemistry studies correlated the experimental and electronic properties of the compounds and identified potential binding modes. The lead compounds exhibited outstanding drug-like properties.