New Imidazole Derivatives: Synthesis, Spectroscopic Characterization, DFT, Biological Activities, and In Silico Study

• Published in: Russian Journal of Physical Chemistry A Vol. 97; no. 13; pp. 3037 - 3049
• Main Authors: Süleymanoğlu, Nevin, Çelik, Fatih, Ustabaş, Reşat, Güler, Halil İbrahim, Şahin, Hüseyin, Direkel, Şahin, Ünver, Yasemin
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01.12.2023; Springer Nature B.V
• Subjects: Benzaldehyde; Carbon 13; Chemistry; Chemistry and Materials Science; Fourier transforms; Imidazole; Imines; NMR; Nuclear magnetic resonance; Physical Chemistry; Structure of Matter and Quantum Chemistry; Synthesis; Schiff base; DFT study; imidazole; in silico study; acetylcholinesterase-antibacterial-leishmanicidal activities
• ISSN: 0036-0244; 1531-863X
• DOI: 10.1134/S0036024423130162

In this study, 4 new compounds containing imidazole ring and Schiff base were synthesized. The imidazole derivatives (1–4) were obtained from the condensation reaction of 3-(1 H -imidazol-1-yl) propan-1-amine and 4-hydroxy benzaldehyde/4-bromo benzaldehyde/4-methoxy benzaldehyde/2,4-dichloro benzaldehyde. Structures of compounds 1 – 4 were characterized by Fourier transform infrared (FTIR), proton and carbon-13 nuclear magnetic resonance ( 1 H- and 13 C-NMR) spectroscopic methods. Theoretical studies of four compounds were carried out by DFT/B3LYP/6-311++G( d,p ) method. The newly synthesized compounds were tested against the enzyme acetylcholinesterase, antibacterial and leishmanicidal activities. The docking study was performed for compounds 3 and 4 with high acetylcholinesterase inhibitory activity to determine possible interactions against human acetylcholinesterase by in silico analysis.