Premium
Synthesis and Microbiological Properties of Novel Bis‐Quaternary Ammonium Compounds Based on Biphenyl Spacer
Author(s) -
Vereshchagin Anatoly N.,
Gordeeva Alexandra M.,
Frolov Nikita A.,
Proshin Pavel I.,
Hansford Karl A.,
Egorov Mikhail P.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900319
Subject(s) - benzalkonium chloride , chemistry , biphenyl , ammonium , pyridinium , cytotoxicity , chloride , nuclear chemistry , stereochemistry , organic chemistry , biochemistry , in vitro
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 C 8 H 17 ‐C 10 H 21 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.