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Vol. 34 No. 5 (2022): Vol 34 Issue 5, 2022

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Synthesis and Antibacterial Evaluation of Three Quaternary Ammonium Surfactants Based on Isatin

https://doi.org/10.14233/ajchem.2022.23577
O. Abdellaoui
Laboratory of Applied Organic Chemistry, Faculty of Science and Technology, University of Sidi Mohamed Ben Abdellah B.P. 2202, Fez, Morocco
M. Chraibi
Laboratory of Microbial Biotechnology and Bioactive Molecules, Faculty of Sciences and Technologies, University of Sidi Mohamed Ben Abdellah. P.O. 2202, Fez Morocco
M.K. Skalli
Laboratory of Applied Organic Chemistry, Faculty of Science and Technology, University of Sidi Mohamed Ben Abdellah B.P. 2202, Fez, Morocco
A. Haoudi
Laboratory of Applied Organic Chemistry, Faculty of Science and Technology, University of Sidi Mohamed Ben Abdellah B.P. 2202, Fez, Morocco
K. Fikri-Benbrahim
Laboratory of Microbial Biotechnology and Bioactive Molecules, Faculty of Sciences and Technologies, University of Sidi Mohamed Ben Abdellah. P.O. 2202, Fez Morocco
Y. Kandri Rodi
Laboratory of Applied Organic Chemistry, Faculty of Science and Technology, University of Sidi Mohamed Ben Abdellah B.P. 2202, Fez, Morocco
A. Mazzah
University of Lille, CNRS, USR 3290, MSAP, Miniaturization for Synthesis, Analysis and Proteomics, F-59000 Lille, France
O. Senhaji
Laboratory of Biomolecular and Macromolecular Chemistry, Faculty of Sciences, University of Moulay Ismail, B.P. 11201, Zitoune, Meknes, Morocco

Corresponding Author(s) : O. Senhaji

o.senhaji@umi.ac.ma

Asian Journal of Chemistry, Vol. 34 No. 5 (2022): Vol 34 Issue 5, 2022

Abstract

In present study, several isatin-derived quaternary ammonium surfactants with different carbon chain lengths were designed and synthesized. They were synthesized by alkylation of indoline-2,3-dione with 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 in an aqueous solution using electrical conductivity. The synthesized surfactants had CMC ranging from 0.01 to 0.012 mol/L. The antibacterial activity of the titer compounds (3a-3c) was evaluated against Gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli), as well as Gram-positive bacteria (Staphylococcus aureus). The surfactant with a long hydrocarbon chain (12 carbons) showed activity against all bacteria tested (minimum inhibitory concentration = 1.25-2.5 mg/mL), whereas those with a short hydrocarbon chain proved to be inactive.

Keywords

Isatin Surfactants Quaternary ammonium compounds Antibacterial activity CMC
Abdellaoui, O., Chraibi, M., Skalli, M., Haoudi, A., Fikri-Benbrahim, K., Kandri Rodi, Y., … Senhaji, O. (2022). Synthesis and Antibacterial Evaluation of Three Quaternary Ammonium Surfactants Based on Isatin. Asian Journal of Chemistry, 34(5), 1274–1278. https://doi.org/10.14233/ajchem.2022.23577
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