Synthesis, structure and in vitro antibacterial activities of new hybrid disinfectants quaternary ammonium compounds: Pyridinium and quinolinium stilbene benzenesulfonates

• Published in: European journal of medicinal chemistry Vol. 45; no. 9; pp. 4199 - 4208
• Main Authors: Chanawanno, Kullapa, Chantrapromma, Suchada, Anantapong, Theerasak, Kanjana-Opas, Akkharawit, Fun, Hoong-Kun
• Format: Journal Article
• Language: English
• Published: ISSY-LES-MOULINEAUX Elsevier Masson SAS 01.09.2010; Elsevier
• Subjects: Antibacterial; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Bacteria - drug effects; Benzenesulfonates - chemical synthesis; Benzenesulfonates - chemistry; Benzenesulfonates - pharmacology; Biological and medical sciences; Chemistry, Medicinal; Crystallography, X-Ray; Disinfectants; Disinfectants - chemical synthesis; Disinfectants - chemistry; Disinfectants - pharmacology; Life Sciences & Biomedicine; Medical sciences; Microbial Sensitivity Tests; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Pyridinium; Pyridinium Compounds - chemistry; Quaternary ammonium compounds (QACs); Quaternary Ammonium Compounds - chemical synthesis; Quaternary Ammonium Compounds - chemistry; Quaternary Ammonium Compounds - pharmacology; Quinolinium; Quinolinium Compounds - chemistry; Science & Technology; Spectrophotometry, Ultraviolet; Spectroscopy, Fourier Transform Infrared; Stilbene; Antibacterial; Disinfectants; Quinolinium; Quaternary ammonium compounds (QACs); Pyridinium; Stilbene; OUTER-MEMBRANE; ANTIMICROBIAL ACTIVITIES; RESISTANCE; BENZALKONIUM CHLORIDE; Organic cation; Molecular structure; X ray diffraction; In vitro; Biological activity; Stilbene derivatives; Sulfonate; Quaternary ammonium compound; Pyridinium compounds; Antibacterial agent; Disinfecting agent; Chemical synthesis; Crystalline structure
• ISSN: 0223-5234; 1768-3254; 1768-3254
• DOI: 10.1016/j.ejmech.2010.06.014

The series of pyridinium ( 1–10) and quinolinium ( 11–20) stilbene benzenesulfonates have been synthesized and their structures were investigated by UV–vis, FT-IR and 1H NMR spectroscopy. In addition, compound 5 was also determined by single crystal X-ray diffraction technique. The antibacterial activity of the synthesized compounds against both Gram-positive and Gram-negative bacteria has been determined. The quinolinium derivatives exhibited two very potent characteristic activities, namely, (i) specific activity to Methicillin-Resistant Staphylococcus aureus and (ii) with broad band spectrum activity. Compounds 11, 13 and 14 are the most active showing broad spectrum antibacterial activity against Gram-positive (Methicillin-Resistant S. aureus, S. aureus, Bacillus subtilis, Vancomycin-Resistant Enterococcus faecalis and E. faecalis) and Gram-negative bacterium ( Shigella sonnei). The MICs of these compounds were found to be better than that of Benzalkonium chloride (BZK), the commercially used disinfectant. The new pyridinium and quinolinium stilbene benzenesulfonates have been synthesized and characterized. All compounds were evaluated for their antibacterial activity against the tested Gram-positive and Gram-negative bacteria using colorimetric assay. [Display omitted]