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Open AccessArticle

Green Accelerated Synthesis, Antimicrobial Activity and Seed Germination Test of Quaternary Ammonium Salts of 1,2-bis(4-pyridyl)ethane

1
Faculty of Sciences and Environment, Department of Chemistry, Physics and Environment, “Dunarea de Jos” University of Galati, 111 Domneasca Street, 800201 Galati, Romania
2
Faculty of Food Science and Engineering, Department of Food Science, Food Engineering and Applied Biotechnology, “Dunarea de Jos” University of Galati, 111 Domneasca Street, 800201 Galati, Romania
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(13), 2424; https://doi.org/10.3390/molecules24132424
Received: 29 May 2019 / Revised: 27 June 2019 / Accepted: 29 June 2019 / Published: 1 July 2019
A family of fifteen quaternary ammonium salts (QAs), bearing the 1,2-bis(4-pyridyl)ethane core, were obtained using for the first time two different green methods, such as microwave (MW) and ultrasounds (US) irradiation, with very good yields and in much shorter times compared to the classical method, and an assay on their antimicrobial action against Escherichia coli (E. coli) was carried out. While 12 to 24 h were required for complete alkylation of 1,2-bis(4-pyridyl)ethane by reactive halogenated derivatives in anhydrous solvent under reflux conditions, MW and US irradiation reduced the reaction time and the desired products were achieved in a few min. One of the aims of this study was to evaluate the antibacterial potential of the synthesized QAs against pathogenic bacteria, along with their impact on germination activity of wheat seeds (Triticum aestivum L.). The antibacterial activity of the QAs against Escherichia coli was explored by determining the minimum inhibitory concentration (MIC). The MIC values varied from 0.312 to 2.5 mg/mL, highlighting the lowest values attained for the derivatives containing methoxy, chlorine and benzofurane functional groups. The viability of aerobic bacteria was determined with the Tetrazolium/Formazan Test, a method that was found to be the best alternative approach with respect to the difuzimetric method. Seeds of Triticum aestivum L. were used for the evaluation of the germination indicators, such as seed germination (SG), the relative seed germination (RSG), the relative radicle growth (RRG), and the seed germination index (GI). The toxicity studies of QAs 1, 4 and 7, at two different concentrations, showed no inhibitory effect on seed germination. View Full-Text
Keywords: quaternary ammonium salts; 1,2-bis(4-pyridyl)ethane; green synthesis; antimicrobial activity; seed germination quaternary ammonium salts; 1,2-bis(4-pyridyl)ethane; green synthesis; antimicrobial activity; seed germination
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Tăbăcaru, A.; Dediu Botezatu, A.V.; Horincar, G.; Furdui, B.; Dinică, R.M. Green Accelerated Synthesis, Antimicrobial Activity and Seed Germination Test of Quaternary Ammonium Salts of 1,2-bis(4-pyridyl)ethane. Molecules 2019, 24, 2424.

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