MMSL 2012, 81(2):76-81 | DOI: 10.31482/mmsl.2012.010

SYNTHESIS OF THE ISOQUINOLINIUM SALTS DIFFERING IN THE LENGTH OF THE SIDE ALKYLATING CHAINOriginal article

Jan Marek ORCID...1,3,4*, Petr Stodůlka2, Ondřej Soukup ORCID...5, Kamil Musílek ORCID...1,5,6, Jiří Cabal1, Kamil Kuča ORCID...2,5
1 Department of Toxicology, Faculty of Military Health Sciences, University of Defence, Trebesska 1575, Hradec Kralove, 50001, Czech Republic
2 Centre of Advanced Studies, Faculty of Military Health Sciences, University of Defence, Trebesska 1575, Hradec Kralove, 50001, Czech Republic
3 Department of Epidemiology, Faculty of Military Health Sciences, University of Defence, Trebesska 1575, Hradec Kralove, 50001, Czech Republic
4 Vakos XT, Pernerova 28a, Prague, 18600, Czech Republic
5 Biomedical Research Center, University Hospital Hradec Kralove
6 Department of Chemistry, Faculty of Science, University of Hradec Kralove, Rokitanskeho 62, 50003, Hradec Kralove, Czech Republic

Cationic tensides are a widespread group of surface active agents. These compounds have lots of applications in various branches of industry and research. Quaternary isoquinolinium salts differing in alkyl chain length are members of a cationic surfactant group with quaternary nitrogen in its structure. The members of this group can be used as micellar catalysts or disinfectants. Decontamination (chemical warfare agents) or disinfection (bacteria or fungi) for very similar compounds was described several times. In this work, the preparation of isoquinoline-derived cationic surfactants differing in the length of the side alkylating chain from C8 to C20 is described. An HPLC method used for distinction of all prepared long-chain isoquinolinium analogues has been successfully developed.

Keywords: isoquinolinium salts; synthesis, HPLC; surfactants; disinfection; decontamination

Received: April 1, 2012; Revised: May 18, 2012; Published: June 8, 2012  Show citation

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Marek, J., Stodůlka, P., Soukup, O., Musílek, K., Cabal, J., & Kuča, K. (2012). SYNTHESIS OF THE ISOQUINOLINIUM SALTS DIFFERING IN THE LENGTH OF THE SIDE ALKYLATING CHAIN. MMSL81(2), 76-81. doi: 10.31482/mmsl.2012.010
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References

  1. Mittal K. L. Solution Behaviour of Surfactants (Theoretical and Applied Aspects). 1 and 2. 1982. New York, Plenum Press. Go to original source...
  2. Balmer, P. Global Atlas of Wastewater Sludge and Biosolids Use and Disposal. 129-132. 1996. UK, ed. P Matthews, IAWQ Scientific and Technical Report No.4, Bourne Press Ltd.
  3. Dyer, D. L.; Gerenratch, K. B.; Wadhams, P. S. Testing a New Alcohol-Free Hand Sanitizer to Combat Infection. AORN journal 1998, 68[2], 239-251. Go to original source... Go to PubMed...
  4. Stepanen, B. N.; Ulitina, T. S.; Zelenkov, V. V. Synthesis of Some Salts of Quaternary Ammonium Bases. Khimiko-Farmatsevticheskii Zhurnal 1974, 8 (10), 21-24. Go to original source...
  5. Nakamura, T.; Thomas, J. K. The Interaction of Alkylammonium Salts with Synthetic Clays - A Fluorescence and Laser Excitation Study. Journal of Physical Chemistry 1986, 90 (4), 641-644. Go to original source...
  6. Rosen M.J. Cationic Surfactants: Organic chemistry, Surfactantscience series 34. Marcel Dekker: New York, 1990.
  7. Menger, F. M.; Littau, C. A. Gemini Surfactants - Synthesis and Properties. Journal of the American Chemical Society 1991, 113 (4), 1451-1452. Go to original source...
  8. Zana R.; Xia J.D. Gemini Surfactants: Synthesis, Interfacial and Solution. Marcel Dekker: New York, 2004; pp.185-210.
  9. Kuca, K.; Bielavska, M.; Cabal, J. et al. Determination of benzalkonium bromide homologues in disinfection products using high-performance liquid chromatography. Analytical Letters 2005;38:673-682. Go to original source...
  10. Semmler, A.; Kohler, H.H. Surface Properties of Alkylpyridinium Chlorides and the Applicability of the Pendant Drop Technique. J. Coll. Interf. Sci. 1999, 218, 137-144. Go to original source... Go to PubMed...
  11. Akbas, H.; Kartal, C.I. Reactive Orange 16-dodecylpyridinium chloride interactions in electrolytic solutions. Spectrochimica Acta Part a-Molecular and Biomolecular Spectroscopy 2006, 65, 95-99. Go to original source... Go to PubMed...
  12. Voss, J. G. Effects of Organic Cations on Gram-Negative Cell Wall and Their Bactericidal Activity with Ethylenediaminetetra-Acetate and Surface Active Agents. Journal of General Microbiology 1967, 48, 391p. Go to original source... Go to PubMed...
  13. Lindstedt, M.; Allenmark, S.; Thompson, R. A.; Edebo, L. Antimicrobial Activity of Betaine Esters, Quaternary Ammonium Amphiphiles Which Spontaneously Hydrolyze Into Nontoxic Components. Antimicrobial Agents and Chemotherapy 1990, 34 (10), 1949-1954. Go to original source... Go to PubMed...
  14. Ng, C. K. L.; Singhal, V.; Widmer, F.; Wright, L. C.; Sorrell, T. C.; Jolliffe, K. A. Synthesis, antifungal and haemolytic activity of a series of bis(pyridinium)alkanes. Bioorganic & Medicinal Chemistry 2007, 15 (10), 3422-3429 Go to original source... Go to PubMed...
  15. Bharate, S. B.; Thompson, C. M. Antimicrobial, Antimalarial, and Antileishmanial Activities of Mono- and Bis-quaternary Pyridinium Compounds. Chemical Biology & Drug Design 2010, 76 (6), 546-551. Go to original source... Go to PubMed...
  16. Acatay, K.; Simsek, E.; Akel, M.; Menceloglu, Y. Z. Electrospinning of low surface energy quaternary ammonium salt containing polymers and their antibacterial activity; SPRINGER: DORDRECHT, 2004.
  17. Wong, Y. L.; Hubieki, M. P.; Curfman, C. L.; Doncel, G. F.; Dudding, T. C.; Savle, P. S.; Gandour, R. D. A structure-activity study of spermicidal and anti-HIV properties of hydroxylated cationic surfactants. Bioorganic & Medicinal Chemistry 2002, 10 (11), 3599-3608. Go to original source... Go to PubMed...
  18. Resuggan, J. C. L. The antibacterial activity of quaternary ammoniumcompounds. Journal of Applied Microbiology 1952, 15 (1), 166-171. Go to original source...
  19. Epstein, J.; Kaminski, J.J.; Bodor, N. et al. Micellar Acceleration of Organophosphate Hydrolysis by Hydroximinomethylpyridinium Type Surfactants. Journal of Organic Chemistry 1978, 43, 2816-2821. Go to original source...
  20. Cabal, J.; Kuca, K.; Micova, J. Kinetics of decomposition of organophosphate Fenitrothion by decontamination foam-making blends. Journal of Applied Biomedicine 2007, 167-170. Go to original source...
  21. Tiwari, S.; Ghosh, K.K.; Marek, J. et al. Cationic Micellar-Catalyzed Hydrolysis of Pesticide Fenitrothion Using alpha-Nucleophiles. Letters in Drug Design & Discovery 2010, 7, 194-199. Go to original source...
  22. Singh, N.; Ghosh, K. K.; Marek, J.; Kuca, K. Hydrolysis of Carboxylate and Phosphate Esters Using Monopyridinium Oximes in Cationic Micellar Media. International Journal of Chemical Kinetics 2011, 43 (10), 569-578 Go to original source...
  23. Ghosh, K. K.; Tiwari, S.; Marek, J.; Kuca, K. New insights into detoxification of chemical warfare simulants and pesticides using micelle mediated systems. Main Group Chemistry 2010, 9 (3-4), 337-353. Go to original source...
  24. Tiwari, S.; Kolay, S.; Ghosh, K. K.; Kuca, K.; Marek, J. Kinetic Study of the Reactions of p-Nitrophenyl Acetate and p-Nitrophenyl Benzoate with Oximate Nucleophiles. International Journal of Chemical Kinetics 2009, 41 (1), 57-64. Go to original source...
  25. Tiwari, S.; Ghosh, K. K.; Marek, J.; Kuca, K. Functionalized surfactant mediated reactions of carboxylate, phosphate and sulphonate esters. Journal of Physical Organic Chemistry 2010, 23 (6), 519-525. Go to original source...
  26. Tiwari, S.; Ghosh, K. K.; Marek, J.; Kuca, K. Cationic Micellar-Catalyzed Hydrolysis of Pesticide Fenitrothion Using alpha-Nucleophiles. Letters in Drug Design & Discovery 2010, 7 (3), 194-199. Go to original source...
  27. Dwars, T.; Paetzold, E.; Oehme, G. Reactions in micellar systems. Angewandte Chemie-International Edition 2005, 44 (44), 7174-7199. Go to original source... Go to PubMed...
  28. Quagliotto, P.; Barbero, N.; Barolo, C. et al. Synthesis and properties of cationic surfactants with tuned hydrophylicity. Journal of Colloid and Interface Science 2009, 340, 269-275. Go to original source... Go to PubMed...
  29. Kuca, K.; Marek, J.; Stodulka, P. et al. Preparation of benzalkonium salts differing in the length of a side alkyl chain. Molecules 2007, 12, 2341-2347. Go to original source... Go to PubMed...
  30. Marek, J.; Stodulka, P.; Cabal, J. et al. Preparation of the Pyridinium Salts Differing in the Length of the N-Alkyl Substituent. Molecules 2010, 15, 1967-1972. Go to original source... Go to PubMed...