Synthesis, Characterization, Molecular Docking, and Investigation of Antibacterial Properties of New Derivatives of 1-H-Phenanthro 9,10-d Imidazole

• Published in: Chemistry & biodiversity Vol. 21; no. 6; p. e202400325
• Main Authors: Mahmoodi, Nosrat O, Rajabi, Anahita, Nyaki, Hadiseh Yazdani, Nahzomi, Hossein Taherpour
• Format: Journal Article
• Language: English
• Published: 01.06.2024
• ISSN: 1612-1880; 1612-1880
• DOI: 10.1002/cbdv.202400325

In this study, several imidazole derivatives in one pot multicomponent reaction from various aldehydes 1(a-z), 9,10-phenanthrenequinone, or benzyl (2), and ammonium acetate (3) were synthesized in the presence of acetic acid (AcOH) under reflux conditions at 120 °C. Also, the photochromic properties of synthesized compounds were investigated in AcOH as a solvent under laboratory conditions at a temperature of 120 °C. Moreover, the antibacterial activity of the synthesized compounds was investigated. The structure of the products was confirmed using FT-IR, UV-Vis, 1H-NMR, and 13CNMR spectroscopy. The antimicrobial activity of these compounds against gram-positive bacteria including Bacillus subtilis (B. subtilis) and gram-negative bacteria including Escherichia coli (E.coli) bacteria was evaluated by the Well diffusion (WD) method, and the compounds 4 o showed significant results for both antibacterial activity. To gain insight into how these compounds interact with two types of targets, i. e., human topoisomerase II alpha (5GWK) and acetylcholinesterase (7AIX), binding calculations have been used that provide significant results for both targets and show that most ligands can effectively bind to cleft nucleotides. Interfere in the first one or be well placed in them. Hydrophobic pocket in the dimension, which can ultimately lead to high scores achieved.In this study, several imidazole derivatives in one pot multicomponent reaction from various aldehydes 1(a-z), 9,10-phenanthrenequinone, or benzyl (2), and ammonium acetate (3) were synthesized in the presence of acetic acid (AcOH) under reflux conditions at 120 °C. Also, the photochromic properties of synthesized compounds were investigated in AcOH as a solvent under laboratory conditions at a temperature of 120 °C. Moreover, the antibacterial activity of the synthesized compounds was investigated. The structure of the products was confirmed using FT-IR, UV-Vis, 1H-NMR, and 13CNMR spectroscopy. The antimicrobial activity of these compounds against gram-positive bacteria including Bacillus subtilis (B. subtilis) and gram-negative bacteria including Escherichia coli (E.coli) bacteria was evaluated by the Well diffusion (WD) method, and the compounds 4 o showed significant results for both antibacterial activity. To gain insight into how these compounds interact with two types of targets, i. e., human topoisomerase II alpha (5GWK) and acetylcholinesterase (7AIX), binding calculations have been used that provide significant results for both targets and show that most ligands can effectively bind to cleft nucleotides. Interfere in the first one or be well placed in them. Hydrophobic pocket in the dimension, which can ultimately lead to high scores achieved.