Jump to ContentJump to Main Navigation
Show Summary Details
More options …

European Pharmaceutical Journal

Acta Facultatis Pharmaceuticae Universitatis Comenianae (formerly)

2 Issues per year


CiteScore 2016: 0.28

SCImago Journal Rank (SJR) 2015: 0.195
Source Normalized Impact per Paper (SNIP) 2015: 0.202

Open Access
Online
ISSN
2453-6725
See all formats and pricing
More options …

Synthesis and antimicrobial properties of binaphthyl derived quaternary ammonium bromides

R. Mikláš
  • Faculty of Pharmacy, Department of Chemical Theory of Drugs, Comenius University in Bratislava
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ N. Miklášová
  • Faculty of Pharmacy, Department of Chemical Theory of Drugs, Comenius University in Bratislava
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ M. Bukovský
  • Faculty of Pharmacy, Department of Cell and Molecular Biology of Drugs, Comenius University in Bratislava
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ F. Devínsky
  • Faculty of Pharmacy, Department of Chemical Theory of Drugs, Comenius University in Bratislava
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2012-08-13 | DOI: https://doi.org/10.2478/v10219-012-0017-5

Synthesis and antimicrobial properties of binaphthyl derived quaternary ammonium bromides

(S)-N-(2-(4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepin-1-yl)ethyl)-N, N-dimethyl-N-dodecyl ammonium bromide (S)-1a and (S)-N-(2-(4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepin-1-yl)ethyl)-N, N-dimethyl-N-tetradecylammonium bromide (S)-1b have been synthesized as optically active quaternary ammonium salts starting from 1,1'-binaphthyl-2,2'-diol. Their antimicrobial activity expressed as minimal inhibition concentration (MIC) was tested against Gram-positive human pathogenic bacteria S. Aureus, Gram-negative bacteria E. coli and human fungal pathogen C. Albicans.

Syntéza A Antimikróbne Vlastnosti Binaftylových Kvartérnych Amónium Bromidov

Vychádzajúc z 1,1'-binaftyl-2,2'-diolu boli pripravené (S)-N-(2-(4,5-dihydro-3H-dinafto[2,1-c:1',2'-e]azepín-1-yl)etyl)-N, N-dimetyl-N-dodecyl amónium bromid (S)-1a a (S)-N-(2-(4,5-dihydro-3H-dinafto[2,1-c:1',2'-e]azepín-1-yl)etyl)-N, N-dimetyl-N-tetradecylamónium bromid (S)-1b. ako opticky aktívne amóniové soli. Bola testovaná ich antimikróbna aktivita, vyjadrená ako minimálna inhibičná koncentrácia (MIC), na Gram-pozitívnu patogénnu baktériu Escherichia coli, Gram-negatívnu baktériu Staphylococcus aureus a kvasinku Candida albicans.

Keywords: quaternary ammonium bromides; antimicrobial activity; binaphthyl

  • Brigham KL, Mezrick B, Christman B, Magnuson M, King G, Berrz LC. Am J Med Sci. 1989;298:278-281.PubMedGoogle Scholar

  • Cai D, Hughes DL, Verhoeven TR, Reider PJ. Resolution of 1,1'-bi-2-naphthol. Organic Synthesis. 2004;10:93.Google Scholar

  • ME, Hayes Cai D, Payack JF, Bender DR, Hughes DL, Verhoeven TR, Reider PJ. (R)-(+)- AND (S) (-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (BINAP). Organic Synthesis. 2004; 10:112.Google Scholar

  • Chanawanno K, Chantrapromma S, Anantapong T, Kanjana-Opas A, Fun H-K. Eur J Med Chem. 2010;45:4199-4208.PubMedGoogle Scholar

  • Cole MR, Li M, El-Zahab B, Janes D, Warner IM. Chem. Biol Drug Des. 2011;78:33-41.CrossrefGoogle Scholar

  • Colomer A, Pinazo A, Manresa MA, Vinardell MP, Mitjans M, Infante MR, Pérez L. Cationic surfactants derived from lysine: effects of their structure and charge type on antimicrobial and hemolytic activities J Med Chem. 2011;54:989-1002.PubMedCrossrefGoogle Scholar

  • Devinsky F, Lacko I, Bittererová F, Mlynarčík D. Quaternary ammonium-salts. 18. Preparation and relationship between structure, IR spectral characteristics and antimicrobial activity of some new bis-quaternary isoesters of 1,5-pentanediammonium dibromides. Chem Pap. 1987:41:803-814.Google Scholar

  • Gilbert P, Al-Taae ANA. Antimicrobial activity of some alkyl-trimethyl ammonium bromides. Lett Appl Microbiol. 1985;1:101-105.CrossrefGoogle Scholar

  • Gilbert P, Moore LE. Cationic antiseptics: diversity of action under a common epithet. J Appl Microbiol. 2005;99: 703-715.CrossrefGoogle Scholar

  • Heinzel JS. The phenomena of resistance to disinfectants and preservatives. In: Industrial biocides. Critical Report on Applied Chemistry. 1988;22:52-67.Google Scholar

  • Jacobs WA, Heidelberger M. The quaternary salts of hexamethylenetetramine I. Substituted benzyl halides and the hexamethylenetetraminuim salts derived therefrom. J Biol Chem. 1915;20:659-683.Google Scholar

  • Jacobs WA, Heidelberger M. The quaternary salts of hexamethylenetetramine II. Monohalogenacetylbenzylamines and their hexamethylenetetraminuim salts. J Biol Chem. 1915;20:685-694.Google Scholar

  • Kano T, Konishi S, Shirikawa S, Maruoka K. Design of new polyamine-based chiral phase-transfer catalyst for the enantioselective synthesis of phenylalanine. Tetrahedron: Asymmetry 2004;15:1243-1245.CrossrefGoogle Scholar

  • Kim YH, Sun G. Functional finishing of acrylic and cationic dyeable fabrics: intermolecular interactions. Textile Res J. 2002;72:1052-1056.Google Scholar

  • La Dow JD, Warnock DC, Hamill KM et al. Eur J Med Chem. 2011;46(9):4219-4226.Google Scholar

  • Lu G, Li X, Zhou Z, Chan WL, Chan ASC. Enantioselective alkynylation of aromatic aldehydes catalyzed by new chiral amino alcohol-based ligands. Tetrahedron: Asymmetry. 2001;12:2147-2152.CrossrefGoogle Scholar

  • Lukáč M, Lacko I, Bukovský M, et al. Synthesis and antimicrobial activity of a series of optically active quaternary ammonium salts derived from phenylalanine. Cent Eur J Chem. 2010;8:194-201.CrossrefGoogle Scholar

  • Mecca T, Superchi S, Giorgio E and Rosini C. 1,1'-Binaphthylazepine-based ligands for asymmetric catalysis. Part 1: Preparation and characterization of some new aminoalcohols and diamines. Tetrahedron: Asymmetry. 2001;12:1225-1233.CrossrefGoogle Scholar

  • Menschutkin Z. Stoechiometrie und Verwandtschaftslehre. Z Phys Chem. 1890;5:589-601.Google Scholar

  • Merianos JJ. Quaternary ammonium antimicrobial compounds. In Disinfection, sterilization, and preservation, 4th ed. Philadephia, 1991: 225-255.Google Scholar

  • Pernak J, Chvala P. Synthesis and anti-microbial activities of choline-like quaternary ammonium chlorides. Eur J Med Chem. 2003;38:1035-1042.CrossrefPubMedGoogle Scholar

  • Pummerer R, Prell E, Rieche A. Ber dtsch chem Ges. 1926;59:2159.Google Scholar

  • Rosini C, Tanturli R, Pertici P, Salvadori P. Enantioselective dihydroxylation of olefins by osmium tetroxide in the presence of an optically active 1,1'-binaphthyl diamine derivative. Tetrahedron: Asymmetry. 1996;7(10):2971-2982.CrossrefGoogle Scholar

  • Semenov VE, Mikhailov AS, Voloshina AD, et al. Eur J Med Chem. 2011;46(9):4715-4724.CrossrefGoogle Scholar

  • Struga M, Kossakowski J, Stefańska J, Zimniak A, Koziol AE. Synthesis and antibacterial activity of bis[2-hydroxy-3-(1,7,8,9,10-pentamethyl-3,5-dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yloxy)-propyl]-dimethyl-ammonium chloride. Eur J Med Chem. 2008;43:1309-1314.Web of ScienceGoogle Scholar

  • Welton T. Chem Rev 1999;99:2071-2083.PubMedGoogle Scholar

  • Wong Y-L, Hubieki MP, Curfaman CL, et al. A structure-activity study of spermicidal and anti-HIV properties of hydroxylated cationic surfactants. Bioorg Med Chem. 2002;10:3599-3608.CrossrefPubMedGoogle Scholar

  • Zhao T, Sun G. Hydrophobicity and antimicrobial activities of quaternary pyridinium salts. J Appl Microbiol. 2008;104:824-830.PubMedCrossrefGoogle Scholar

About the article


Published Online: 2012-08-13

Published in Print: 2012-01-01


Citation Information: Acta Facultatis Pharmaceuticae Universitatis Comenianae, ISSN (Print) 0301-2298, DOI: https://doi.org/10.2478/v10219-012-0017-5.

Export Citation

This content is open access.

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
Megan C. Jennings, Kevin P. C. Minbiole, and William M. Wuest
ACS Infectious Diseases, 2015, Volume 1, Number 7, Page 288
[2]
R. Mikláš, N. Miklášová, M. Bukovský, B. Horváth, J. Kubincová, and F. Devínsky
European Journal of Pharmaceutical Sciences, 2014, Volume 65, Page 29

Comments (0)

Please log in or register to comment.
Log in