Synthesis and antimicrobial properties of binaphthyl derived quaternary ammonium bromides

Mikláš, R.; Miklášová, N.; Bukovský, M.; Devínsky, F.

doi:10.2478/v10219-012-0017-5

Abstract

(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.

References

Brigham KL, Mezrick B, Christman B, Magnuson M, King G, Berrz LC. Am J Med Sci. 1989;298:278-281.10.1097/00000441-198910000-00013
Search in Google Scholar
Cai D, Hughes DL, Verhoeven TR, Reider PJ. Resolution of 1,1'-bi-2-naphthol. Organic Synthesis. 2004;10:93.
Search in 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.
Search in Google Scholar
Chanawanno K, Chantrapromma S, Anantapong T, Kanjana-Opas A, Fun H-K. Eur J Med Chem. 2010;45:4199-4208.10.1016/j.ejmech.2010.06.014
Search in Google Scholar
Cole MR, Li M, El-Zahab B, Janes D, Warner IM. Chem. Biol Drug Des. 2011;78:33-41.10.1111/j.1747-0285.2011.01114.x
Search in Google 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;54:989-1002.10.1021/jm101315k
Search in Google 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.
Search in Google Scholar
Gilbert P, Al-Taae ANA. Antimicrobial activity of some alkyl-trimethyl ammonium bromides. Lett Appl Microbiol. 1985;1:101-105.10.1111/j.1472-765X.1985.tb01498.x
Search in Google Scholar
Gilbert P, Moore LE. Cationic antiseptics: diversity of action under a common epithet. J Appl Microbiol. 2005;99: 703-715.10.1111/j.1365-2672.2005.02664.x
Search in Google Scholar
Heinzel JS. The phenomena of resistance to disinfectants and preservatives. In: Industrial biocides. Critical Report on Applied Chemistry. 1988;22:52-67.
Search in 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.
Search in Google Scholar
Jacobs WA, Heidelberger M. The quaternary salts of hexamethylenetetramine II. Monohalogenacetylbenzylamines and their hexamethylenetetraminuim salts. J Biol Chem. 1915;20:685-694.10.1016/S0021-9258(18)88226-6
Search in 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;15:1243-1245.10.1016/j.tetasy.2004.02.023
Search in Google Scholar
Kim YH, Sun G. Functional finishing of acrylic and cationic dyeable fabrics: intermolecular interactions. Textile Res J. 2002;72:1052-1056.10.1177/004051750207201203
Search in Google Scholar
La Dow JD, Warnock DC, Hamill KM et al. Eur J Med Chem. 2011;46(9):4219-4226.10.1016/j.ejmech.2011.06.02621794958
Search in 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;12:2147-2152.10.1016/S0957-4166(01)00384-6
Search in Google 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;8:194-201.10.2478/s11532-009-0126-8
Search in Google 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;12:1225-1233.10.1016/S0957-4166(01)00199-9
Search in Google Scholar
Menschutkin Z. Stoechiometrie und Verwandtschaftslehre. Z Phys Chem. 1890;5:589-601.10.1515/zpch-1890-0546
Search in Google Scholar
Merianos JJ. Quaternary ammonium antimicrobial compounds. In Disinfection, sterilization, and preservation, 4^th ed. Philadephia, 1991: 225-255.
Search in Google Scholar
Pernak J, Chvala P. Synthesis and anti-microbial activities of choline-like quaternary ammonium chlorides. Eur J Med Chem. 2003;38:1035-1042.10.1016/j.ejmech.2003.09.004
Search in Google Scholar
Pummerer R, Prell E, Rieche A. Ber dtsch chem Ges. 1926;59:2159.10.1002/cber.19260590881
Search in 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):2971-2982.10.1016/0957-4166(96)00388-6
Search in Google Scholar
Semenov VE, Mikhailov AS, Voloshina AD, et al. Eur J Med Chem. 2011;46(9):4715-4724.10.1016/j.ejmech.2011.05.03421652122
Search in Google 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;43:1309-1314.10.1016/j.ejmech.2007.08.01417950957
Search in Google Scholar
Welton T. Chem Rev 1999;99:2071-2083.10.1021/cr980032t11849019
Search in Google 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;10:3599-3608.10.1016/S0968-0896(02)00245-6
Search in Google Scholar
Zhao T, Sun G. Hydrophobicity and antimicrobial activities of quaternary pyridinium salts. J Appl Microbiol. 2008;104:824-830.10.1111/j.1365-2672.2007.03616.x17973914
Search in Google Scholar

Synthesis and antimicrobial properties of binaphthyl derived quaternary ammonium bromides

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