Conventional versus ultrasound and microwave assisted synthesis: Some new environmentally friendly functionalized picolinium-based ionic liquids with potential antibacterial activity

Messali, Mouslim

doi:10.1515/acph-2015-0028

Abstract

A green chemistry approach has been adopted for the synthesis of thirty-four new picolinium-based ionic liquids using microwave (MW) and ultrasound (US) irradiation as well as conventional thermal heating. Their structures were confirmed by FT-IR, ¹H NMR, ¹³C NMR, ¹¹B NMR, ¹⁹F NMR, ³¹P NMR, mass spectra and elemental analyses. The antimicrobial profile of the novel ionic liquids was evaluated and the minimum inhibitory concentration (MIC) showed their moderate to low antimicrobial activity against eight types of human pathogens.

References

1. J. H. Davis, Jr., Task-specific ionic liquids, Chem. Lett. 33 (2004) 1072–1079; DOI: 10.1246/cl.2004.1072.10.1246/cl.2004.1072
Search in Google Scholar
2. J. H. Wang, D. H. Cheng, X. Y. Chen, Z. Du and Z. L. Fang, Direct extraction of double stranded DNA into ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate and its quantification, Anal. Chem. 79 (2007) 620–625; DOI: 10.1021/ac061145c.10.1021/ac061145c
Search in Google Scholar
3. F. Endres, Ionic liquids: solvents for the electrodeposition of metals and semiconductors, Chem. Phys. Chem. 3 (2002) 144–154; DOI: 10.1002/1439–7641(20020215)3:2.
Search in Google Scholar
4. Y. F. Lin and I. W. Sun, Electrodeposition of zinc from a Lewis acidic zinc chloride-1-ethyl-3-methylimidazolium chloride molten salt, Electrochim. Acta44 (1999) 2771–2777; DOI: 10.1016/S0013-4686(99)00003-1.10.1016/S0013-4686(99)00003-1
Search in Google Scholar
5. M. A. M. Ibrahim, M. Messali, Z. Moussa, A. Y. Alzahrani, S. N. Alamry and B. Hammouti, Corrosion inhibition of carbon steel by imidazolium and pyridinium cations ionic liquids in acidic environment, Port. Electrochim. Acta29 (2013) 375–389; DOI: 10.4152/pea.201106375.10.4152/pea.201106375
Search in Google Scholar
6. M. Messali, A green microwave-assisted synthesis, characterization and comparative study of new pyridazinium-based ionic liquids derivatives towards corrosion of mild steel in acidic environment, J. Mater. Environ. Sci. 2 (2011) 174–185.
Search in Google Scholar
7. M. Messali and M. A. M. Asiri, A green ultrasound-assisted access to some new 1-benzyl-3-(4-phenoxybutyl) imidazolium-based ionic liquids derivatives – potent agents inhibitors against corrosion of mild steel in acidic environment, J. Mater. Environ. Sci.4 (2013) 770–785.
Search in Google Scholar
8. A. Zarrouk, M. Messali, M. R. Aouad, H. Zarrok, R. Salghi, B. Hammouti, A. Chetouani and S. S. Al-Deyab, Some new ionic liquids derivatives: Synthesis, characterization and comparative study towards corrosion of C-steel in acidic media, J. Chem. Pharm. Res. 4 (2012) 3427–3436.
Search in Google Scholar
9. A. Zarrouk, M. Messali, H. Zarrok, R. Salghi, A. Al-Sheikh Ali, B. Hammouti, S. S. Al-Deyab and F. Bentiss, Synthesis, characterization and comparative study of new functionalized imidazolium-based ionic liquids derivatives towards corrosion of C38 steel in molar hydrochloric acid, Int. J. Electrochem. Sci. 7 (2012) 6998–7015.
Search in Google Scholar
10. S. Takahashi, N. Koura, S. Kohara, M. L. Saboungi and L. A. Curtiss, Technological and scientific issues of room-temperature molten salts, Plasmas Ions2 (2009) 91–105; DOI: 10.1016/S1288-3255(99)00105-7.10.1016/S1288-3255(99)00105-7
Search in Google Scholar
11. J. F. Brennecke and E. J. Magin, Ionic liquids: innovative fluids for chemical processing, AIChE J.47 (2001) 2384–2389; DOI: 10.1002/aic.690471102.10.1002/aic.690471102
Search in Google Scholar
12. F. Shi, Y. Gu, Q. Zhang and Y. Deng, Development of ionic liquids as green reaction media and catalysts, Catal. Surv. Asia8 (2004) 179–186; DOI: 10.1023/B:CATS.0000038536.55980.
Search in Google Scholar
13. R. F. De Souza, J. C. Padilha, R. S. Goncalves and J. L. Rault-Berthelot, Dialkyl imidazolium ionic liquids as electrolytes for hydrogen production from water electrolysis, Electrochem. Commun.8 (2006) 211–216; DOI: 10.1016/j.elecom.2005.10.036.10.1016/j.elecom.2005.10.036
Search in Google Scholar
14. P. Kubisa, Application of ionic liquids as solvents for polymerization processes, Prog. Polym. Sci. 29 (2004) 3–12; DOI: 10.1016/j.progpolymsci.2003.10.002.10.1016/j.progpolymsci.2003.10.002
Search in Google Scholar
15. R. Kawano, H. Matsui, C. Matsuyama, A. Sato, M. A. B. H. Susan, N. Tanabe and M. Watanabe, High performance dye-sensitized solar cells using ionic liquids as their electrolytes, J. Photochem. Photobiol. A164 (2004) 87–92; DOI: 10.1016/j.jphotochem.2003.12.019.10.1016/j.jphotochem.2003.12.019
Search in Google Scholar
16. G. Zbancioc, A. M. Zbancioc and I. I. Mangalagiu, Ultrasound and microwave assisted synthesis of dihydroxyacetophenone derivatives with or without 1,2-diazine skeleton, Ultrason. Sonochem.21 (2014) 802–811; DOI: 10.1016/j.ultsonch.2013.09.012.10.1016/j.ultsonch.2013.09.01224139876
Search in Google Scholar
17. D. Garella, S. Tagliapietra, V. P. Mehta, E. Van Der Eycken and G. Cravotto, Straightforward functionalization of 3,5-dichloro-2-pyrazinones under simultaneous microwave and ultrasound irradiation, Synthesis2010, 136–140; DOI: 10.1055/s-0029-1217065.10.1055/s-0029-1217065
Search in Google Scholar
18. V. Bejan, D. Mantu and I. I. Mangalagiu, Ultrasound and microwave assisted synthesis of isoindolo-1,2-diazine: A comparative study, Ultrason. Sonochem. 19 (2012) 999–1002; DOI: 10.1016/j.ultsonch.2012.02.012.10.1016/j.ultsonch.2012.02.01222464108
Search in Google Scholar
19. I. I. Mangalagiu, Recent achievements in the chemistry of 1,2-diazines, Curr. Org. Chem. 15 (2011) 730–752; DOI: 10.2174/138527211794519050.10.2174/138527211794519050
Search in Google Scholar
20. G. Zbancioc and I. I. Mangalagiu, Pyrrolopyridazine derivatives as blue organic luminophores: synthesis and properties. Part 2, Tetrahedron66 (2010) 278–282; DOI: 10.1016/j.tet.2009.10.110.10.1016/j.tet.2009.10.110
Search in Google Scholar
21. A. Loupy, A. Petit, J. Hamelin, F. Texier-Boulier, P. Jacquault and D. Mathe, New solvent free organic synthesis using focused microwaves, Synthesis1998, 1213–1234; DOI: 10.1055/s-1998–6083.10.1055/s-1998-6083
Search in Google Scholar
22. M. Messali, An efficient and green sonochemical synthesis of some new eco-friendly functionalized ionic liquids, Arab. J. Chem. 7 (2014) 63–70; DOI: 10.1016/j.arabjc.2013.08.023.10.1016/j.arabjc.2013.08.023
Search in Google Scholar
23. M. Messali and S. A. Ahmed, A green microwave-assisted synthesis of new pyridazinium-based ionic liquids as an environmentally friendly alternative, Green Sustain. Chem. 1 (2011) 70–75; DOI: 10.4236/gsc.2011.13012.10.4236/gsc.2011.13012
Search in Google Scholar
24. M. Messali, A facile and green microwave-assisted synthesis of new functionalized picolinium-based ionic liquids (in press); DOI: 10.1016/j.arabjc.2011.06.030.10.1016/j.arabjc.2011.06.030
Search in Google Scholar
25. J. R. Carreon, K. M. Stewart, K. P. Mahon, S. Shin and S. O. Kelley, Cyanine dye conjugates as probes for live cell imaging, Bioorg. Med. Chem. Lett.17 (2007) 5182–5185; DOI: 10.1016/j.bmcl.2007.06.097.10.1016/j.bmcl.2007.06.09717646099
Search in Google Scholar
26. M. Messali, Z. Moussa, A. Y. Alzahrani, M. Y. El-Naggar, A. S. El Douhaibi, Z. M. A. Judeh and B. Hammouti, Synthesis, characterization, antimicrobial activity of new green-chemistry-friendly ionic liquids, Chemosphere91 (2013) 1627–1634; DOI: 10.1016/j.chemosphere.2012.12.062.10.1016/j.chemosphere.2012.12.06223357867
Search in Google Scholar
27. M. Messali, M. R. Aouad, A. A. Ali, N. Rezki, T. Ben Hadda and B. Hammouti, Synthesis, characterization, and POM analyses of novel bioactive imidazolium-based ionic liquids, Med. Chem. Res.24 (2015) 1387–1395; DOI: 10.1007/s00044-014-1211-x.10.1007/s00044-014-1211-x
Search in Google Scholar
28. Clinical and Laboratory Standards Institute (CLSI), Document M26-A, Methods of determining bactericidal activity of antimicrobial agents for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved guideline, Wayne (PA) 1999.
Search in Google Scholar
29. H. Nomura, Y. Isshiki, K. Sakuda, K. Sakuma and S. Kondo, The antibacterial activity of compounds isolated from Oakmoss against Legionella pneumophila and other Legionella spp, Biol. Pharm. Bull.35 (2012) 1560–1567; DOI: 10.1007/s11064-012-0751-z.10.1007/s11064-012-0751-z22447574
Search in Google Scholar
30. Clinical and Laboratory Standards Institute (CLSI), Document M7-A5, Methods for antibacterial susceptibility test for bacteria that grow aerobically. Approved standard, 5th ed., Wayne (PA) 2000.
Search in Google Scholar

Conventional versus ultrasound and microwave assisted synthesis: Some new environmentally friendly functionalized picolinium-based ionic liquids with potential antibacterial activity

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