Open AccessSynthesis and Antibacterial Evaluation of Three Quaternary Ammonium Surfactants Based on Isatin
Author(s) -
Omar Abdellaoui,
Marwa Chraibi,
M.K. Skalli,
A. Haoudi,
Kawtar Fikri-Benbrahim,
Youssef Kandri Rodi,
Ahmed Mazzah,
O. Senhaji
Publication year - 2022
Publication title -
asian journal of chemistry/asian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.145
H-Index - 34
eISSN - 0975-427X
pISSN - 0970-7077
DOI - 10.14233/ajchem.2022.23577
Subject(s) - chemistry , isatin , nuclear chemistry , critical micelle concentration , micelle , ammonium , antibacterial activity , pulmonary surfactant , bacteria , carbon 13 nmr , hydrocarbon , alkylation , proton nmr , aqueous solution , organic chemistry , biochemistry , biology , genetics , catalysis
In present study, several isatin-derived quaternary ammonium surfactants with different carbon chainlengths were designed and synthesized. They were synthesized by alkylation of indoline-2,3-dionewith various dibromo-alkanes, then quaternization with trimethylamine. Nuclear magnetic resonance(1H NMR, 13C NMR) and mass spectroscopy were employed to examine their chemical structures.Further, the critical micelle concentrations (CMC) value of surfactants synthesized was determined inan aqueous solution using electrical conductivity. The synthesized surfactants had CMC ranging from0.01 to 0.012 mol/L. The antibacterial activity of the titer compounds (3a-3c) was evaluated againstGram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli), as well as Gram-positivebacteria (Staphylococcus aureus). The surfactant with a long hydrocarbon chain (12 carbons) showedactivity against all bacteria tested (minimum inhibitory concentration = 1.25-2.5 mg/mL), whereasthose with a short hydrocarbon chain proved to be inactive.