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Synthesis and Microbiological Properties of Novel Bis‐Quaternary Ammonium Compounds Based on Biphenyl Spacer Full article

Journal European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690
Output data Year: 2019, Volume: 2019, Number: 26, Pages: 4123-4127 Pages count : 5 DOI: 10.1002/ejoc.201900319
Authors Vereshchagin Anatoly N. 1 , Gordeeva Alexandra M. 2,1 , Frolov Nikita A. 1 , Proshin Pavel I. 2,1 , Hansford Karl A. 3 , Egorov Mikhail P. 1
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Procpekt, 119991 Moscow, Russia
2 Higher Chemical College of Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya square 9, 125047 Moscow, Russia
3 Hansford Institute for Molecular Bioscience, The University of Queensland, 4072 Brisbane, Queensland, Australia

Abstract: Novel gemini (tail-head-spacer-head-tail) bis-quaternary ammonium compounds (bis-QACs) with a biphenyl spacer between two pyridinium heads were synthesized and compared with commonly used antiseptics such as benzalkonium chloride (BAC) and chlorhexidine digluconate (CHG). The series of compounds showed high inhibitory activity against five bacterial strains and two fungi. The compounds, which contain C8H17-C10H21 aliphatic tails best within the series. A counterion change does not affect MIC in general. Cytotoxicity on human embryonic kidney cells and haemolysis were also investigated. For bis-QACs cytotoxic effect was lower than for 3,3′-[1,4-phenylenebis(oxy)]bis(1-dodecylpyridinium) dibromide (3PHBO-12), that is their closest structural analogue, and for BAC.
Cite: Vereshchagin A.N. , Gordeeva A.M. , Frolov N.A. , Proshin P.I. , Hansford K.A. , Egorov M.P.
Synthesis and Microbiological Properties of Novel Bis‐Quaternary Ammonium Compounds Based on Biphenyl Spacer
European Journal of Organic Chemistry. 2019. V.2019. N26. P.4123-4127. DOI: 10.1002/ejoc.201900319 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000475679400004
Scopus: 2-s2.0-85067680524
OpenAlex: W2946561417
Citing:
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OpenAlex 22
Scopus 22
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