Synthesis and antimicrobial activities of some new sulfonyl phenoxides

Abstract

Four new sulfonyl phenoxides were synthesized through O-sulfonylation reaction of phenolic compounds with 5-chloro-1-ethyl-2-methylimidazole-4-sulfonyl chloride in good yield. FT-IR, 1H-NMR, 13C-NMR, and DEPT 135 NMR were carried out to characterize and the thin layer chromatography (TLC) confirm the purity. Antimicrobial activities of the sulfonyl phenoxides against Gram-positive (methicillin-susceptible Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, and Bacillus subtilis), Gram-negative (Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae), and Candida albicans were carried out using the standard microbiological method. The antimicrobial activities were referenced to ciprofloxacin and itraconazole, antibacterial and antifungal drug respectively. The in vitro antimicrobial studies of 5-chloro-1-ethyl-2-methyl-1H-imidazole-4-sulfonyl(4-chloro-3-methyl)phenoxide and 5-chloro-1-ethyl-2-methyl-1H-imidazole-4-sulfonyl-2-methylphenoxide showed moderate activity against C. albicans. The four sulfonyl phenoxides had weak activities against Gram-positive and Gram-negative bacteria.

Keywords: Sulfonyl phenoxides, Antimicrobial, Phenolic compounds, O-Sulfonylation reaction