SYNTHESIS AND CHARACTERIZATION OF 2,4-di-tert-butyl-6-((2-(4-nitrophenyl)-1H-imidazol-3-yl)ethyl)imino)methyl)phenol FROM 1-(4-nitrophenyl)-1H-imidazole AND 2-(((2-bromoethyl)imino)methyl)-4,6-di-tert-butylphenol AND THEIR BIOLOGICAL STUDIES

Abstract

Bacterial and fungal infections remain a major challenge in healthcare systems worldwide, necessitating the continuous exploration of novel therapeutic agents. This study reports the synthesis, characterization, and antimicrobial evaluation of three compounds: 1-(4-nitrophenyl)-1H-imidazole (Compound 1), 2-(((2-bromoethyl)imino)methyl)-4,6-di-tert-butylphenol (Compound 2), and 2,4-di-tert-butyl-6-((2-(4-nitrophenyl)-1H-imidazol-3-yl)ethyl)imino)methyl)phenol (Compound 3). Syntheses were achieved with 70-87% yields, and structures were confirmed via 1H-NMR, 13C-NMR, IR, and LCMS. Antimicrobial assays revealed that Compound 2 exhibited the strongest antibacterial activity, especially against Klebsiella oxytoca (zone of inhibition: 23 mm, MIC: 500 µg/mL). Compound 1 showed moderate dual activity, notably against Mucor spp. (zone of inhibition: 12 mm MIC: 500 µg/mL). Despite their promising activity, the compounds demonstrated higher MBC and MFC values, indicating primarily bacteriostatic and fungistatic effects. This work provides insights into the structure-activity relationships of these compounds, highlighting their potential as lead structures for further antimicrobial development.