New Imidazole Derivatives: Synthesis, Spectroscopic Characterization, DFT, Biological Activities, and In Silico Study
Nevin Süleymanoğlua,*, Fatih Çelikb, Reşat Ustabaşc, Halil İbrahim Gülerd,
Hüseyin Şahine, Şahin Direkelf, and Yasemin Ünverb
a Graduate School of Natural and Applied Sciences, Advanced Technologies, Gazi University, Ankara, 06500 Turkey
b Department of Chemistry, Faculty of Sciences, Karadeniz Technical University, Trabzon, 61080 Turkey
c Department of Mathematics and Science Education, Educational Faculty, Ondokuz Mayıs University,
Kurupelit, Samsun, 55139 Turkey
d Department of Molecular Biology and Genetics, Faculty of Science, Karadeniz Technical University, Trabzon, 61080 Turkey
e Giresun University, Espiye Vocational School, Espiye, 26800 Giresun Turkey
f Department of Medical Microbiology, Faculty of Medicine, Giresun University, Giresun, 28100 Turkey
Correspondence to: * e-mail: nevinseylan@gmail.com
Received 16 December, 2022
Abstract—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-(1H-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 (1H- and 13C-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.
Abstract—
Keywords: imidazole, Schiff base, DFT study, acetylcholinesterase-antibacterial-leishmanicidal activities, in silico study
DOI: 10.1134/S0036024423130162