Quaternary ammonium salts substituted by 5‐phenyl‐1,3,4‐oxadiazole‐2‐thiol as novel antibacterial agents with low cytotoxicity
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 unsurpa...
Saved in:
Published in | Chemical biology & drug design Vol. 90; no. 5; pp. 943 - 952 |
---|---|
Main Authors | , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
HOBOKEN
Wiley
01.11.2017
|
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | 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, 8g 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.
Twenty‐one novel 5‐phenyl‐1,3,4‐oxadiazole‐2‐thiol (POT) substituted QAS were prepared with the unsurpassed antibacterial abilities. POT and flexible dihydroxyethyl group in QAS are necessary for activity. SEM and TEM images of E. coli morphologies of 8d show it can adhere to membrane surfaces to inhibit bacterial growth by disrupting peptidoglycan formation and releasing bacterial cytoplasm. |
---|---|
Bibliography: | Funding information The National Natural Science Foundation of China, Grant/Award Number: 21402010; the Foundation of Shandong province, Grant/Award Number: ZR2013BM022; 2014CGZH1316; 2015GGX102013; the Foundation of Yantai city, Grant/Award Number: 2016ZH078, 2014ZH092 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1747-0277 1747-0285 |
DOI: | 10.1111/cbdd.13020 |