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

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 act...

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Published inEuropean 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
LanguageEnglish
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
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Abstract 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]
AbstractList 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]
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 (1)H 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 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 (1)H 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 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 (1)H 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 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 H-1 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. (C) 2010 Elsevier Masson SAS. All rights reserved.
Author Fun, Hoong-Kun
Chantrapromma, Suchada
Anantapong, Theerasak
Kanjana-Opas, Akkharawit
Chanawanno, Kullapa
Author_xml – sequence: 1
  givenname: Kullapa
  surname: Chanawanno
  fullname: Chanawanno, Kullapa
  organization: Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
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  givenname: Suchada
  surname: Chantrapromma
  fullname: Chantrapromma, Suchada
  email: suchada.c@psu.ac.th
  organization: Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
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  givenname: Theerasak
  surname: Anantapong
  fullname: Anantapong, Theerasak
  organization: Department of Industrial Biotechnology, Faculty of Agro-Industry, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
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  givenname: Akkharawit
  surname: Kanjana-Opas
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  givenname: Hoong-Kun
  surname: Fun
  fullname: Fun, Hoong-Kun
  organization: X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM Penang, Malaysia
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Issue 9
Keywords 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
Language English
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2010 Elsevier Masson SAS. All rights reserved.
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Snippet The series of pyridinium ( 1–10) and quinolinium ( 11–20) stilbene benzenesulfonates have been synthesized and their structures were investigated by UV–vis,...
The series of pyridinium (1-10) and quinolinium (11-20) stilbene benzenesulfonates have been synthesized and their structures were investigated by UV-vis,...
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SubjectTerms 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
Title Synthesis, structure and in vitro antibacterial activities of new hybrid disinfectants quaternary ammonium compounds: Pyridinium and quinolinium stilbene benzenesulfonates
URI https://dx.doi.org/10.1016/j.ejmech.2010.06.014
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