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Quaternary ammonium salts substituted by 5‐phenyl‐1,3,4‐oxadiazole‐2‐thiol as novel antibacterial agents with low cytotoxicity
Author(s) -
Wang ChunHua,
Xie XianRui,
Liu WenShuai,
Hou GuiGe,
Sun JuFeng,
Zhao Feng,
Cong Wei,
Li HongJuan,
Xin WenYu
Publication year - 2017
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.13020
Subject(s) - antibacterial activity , chemistry , cytotoxicity , proteus vulgaris , thiol , escherichia coli , ammonium , antimicrobial , stereochemistry , nuclear chemistry , bacteria , bacterial cell structure , organic chemistry , biochemistry , biology , genetics , gene , in vitro
Twenty‐one novel 5‐phenyl‐1,3,4‐oxadiazole‐2‐thiol ( POT ) substituted N ‐hydroxyethyl quaternary ammonium salts ( 6a–g , 7a–g , 8a–g ) were prepared and characterized by FTIR , NMR , and elemental analysis. Compounds 6a , 6c , and 8a were confirmed by X ‐ray single‐crystal diffraction. They display the unsurpassed antibacterial activity against Staphylococcus aureus , α ‐H‐tococcus , Escherichia coli , P. aeruginosa , Proteus vulgaris , Canidia Albicans , especially 6g , 7g , 8 g with dodecyl group. Compounds 8a–d with N,N ‐dihydroxyethyl and POT groups display unsurpassed antibacterial activity and non‐toxicity. The structure–activity relationships indicate that POT and flexible dihydroxyethyl group in QAS are necessary for antibacterial activity and cytotoxicity. SEM and TEM images of E. coli morphologies of 8d show the antibacterial agents can adhere to membrane surfaces to inhibit bacterial growth by disrupting peptidoglycan formation and releasing bacterial cytoplasm from cell membranes.