Synthesis and antimicrobial activities of some quaternary morpholinium chlorides

• Autorzy: Brycki B , Dega-Szafran Z. , Mirska I.
• Języki publikacji: EN

Abstrakty

EN

The synthesis and antimicrobial activity of 31 morpholinium chlorides, divided into five series depending on the substituents attached to the nitrogen atom, N-carboxyalkyl-morpholinium chlorides (la-e), N-carbalkoxymethyl-N-methyl-morpholinium chlorides (2a-f), N-carbethoxymethyl-N-alkyl-morpholinium chlorides (3a-g), N-carbalkoxymethyl-N-dodecyl-morpholinium chlorides (4a-f) and N-car-boxymethyl-N-alkyl-morpholinium chlorides (5a-g) is reported. The compounds investigated were tested for antimicrobial activity against Staphylococcus aureus, Escherichia coli, Proteus vulgaris, Pseudomonas aeruginosa, Candida albicans and Trichophyton menthagwphytes. The most active are compounds with a long N-alkyl group and with the substituent CH2COOCnH2n-1 (n = 8-16).

Słowa kluczowe

EN

antimicrobial activity; synthesis; quaternary morpholinium chloride; quaternary ammonium compound; antimicrobial property; Staphylococcus aureus; Escherichia coli; Pseudomonas aeruginosa; Candida albicans; Trichophyton mentagrophytes; N-alkyl group

• Wydawca: -
• Czasopismo: Polish Journal of Microbiology
• Rocznik: 2010
• Tom: 59
• Numer: 1
• Opis fizyczny: p.49-53,fig.,ref.

Twórcy

autor

Brycki B

• Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland

autor

Dega-Szafran Z.

autor

Mirska I.

Bibliografia

• Block S.S. (ed.) 2001. Disinfection, Sterilization, and Preservation, (ed.:), Lippincott Williams and Wilkins, 5th Edition, Philadelphia USA.
• Dega-Szafran Z., Gąszczyk I., Maciejewska D., Szafran M., Tykarska E. and Wawer I. 2001. ¹³C CP MAS NMR, FTIR X-Ray diffraction and PM3 studies of some N-(w-carboxyalkyl) morpholine hydrohalides. J. Mol. Struct. 560: 261-273.
• Dega-Szafran Z., Antkowiak A., Grundwald-Wyspiańska M., Nowak E., Gdaniec M. and Kosturkiewicz Z. 2002a. Structure and hydrogen bonding in a 3:2 inclusion compound of N-methyl-morpholine betaine hydrochloride with acetone. J. Mol. Struct. 605: 325-330.
• Dega-Szafran Z., Antkowiak A., Grundwald-Wyspiańska M., Nowak E. and Kosturkiewicz Z. 2002b. Crystal structure of bis(N-methylmorpholine betaine) hydrochloride, FTIR and NMR studies of 1:1 and 2:1 complexes of N-methylmorpholine betaine with mineral acids. J. Mol. Struct. 605: 309-317.
• Dega-Szafran Z., Dulewicz E. and Brycki B. 2007. Synthesis and characterization of 1 -carbalkoxymethyl-4-hydroxy-1 -methyl-piperidinium chlorides. ARKIVOC, part vi: 90-102 (http:/www. Arkat-usa.org).
• Domingo X. 1996. Betaines. In Lomax E.G. (ed) Amphoteric Surfactants, Marcel Dekker Inc., New York USA Vol. 59, pp. 76-190.
• Fraise A.P., Lambert P.A. and Maillard J-Y. (eds). 2004. Russell, Hugo and Ayliffe's Principles and Practice of Disinfection, Preservation and Sterilization. Blackwell Publishing, 4th Edition, Maiden USA.
• Fredell D.L. 1994. Biological Properties and Applications of Cationic Surfactants in Cationic Surfactants (Analytical and Biological Evaluation) Cross J. and Singer E..T. (eds), Marcel Dekker Inc., New York USA, Vol. 53, 31-60.
• Manivannan G. (ed.) 2008. Disinfection and Decontamination: Principles, Applications and Related Issues, CRC Press Taylor & Francis Group, Boca Raton USA.
• Mosca A., Russo F. and Miragliotta G. 2006. In vitro antimicrobial activity of benzalkonium chloride against clinical isolates of Streptococcus agalactiae. 57: 566-568.
• Paulus W. (ed.) 2005. Directory of Microbiocides for the Protection of Materials. A. Handbook, Springer, Dordrecht, The Netherlands.
• Shelton R.S., Van Campen M.G., Tilford C.H., Lang H.C., Nisonger L., Bandelin F.J. and Rubenkoenig H.L. 1946. Quaternary Ammonium Salts as Germicides. J. Am. Chem. Sot: 68: 753-759.
• Smith D.R., Maienthal M. and Eifert R.L. 1951. Quaternary Ammonium Salts of Heterocyclic Bases. J. Am. Chem. Soc: 73: 2964-2965.
• Takasaki A., Hashida T., Fujiwara S., Kato K. and Nishihara T. 1994. Bactericidal action of a quaternary ammonium disinfectant, didecyldimethyl ammonium chloride, against Staphylococcus aureus. Jpn. J. Toxicol Environ. Health, 40: 344-350.
• Woźniak E., Morzymas A., Czarny A., Kocięba B., Różycka-Roszak B., Dega-Szafran Z., Dulewicz E. and Petryna M. 2004. Antimicrobial activity of N-alkoxycarbonylmethyl-N-alkylpiperidinium chlorides Z. Naturforsch. 59c: 782-786.