Syntheses and antimicrobial activities of a series of new bis-quaternary ammonium compounds

被引:114
|
作者
Kourai, Hiroki [1 ]
Yabuhara, Tadao [1 ]
Shirai, Akihiro [1 ]
Maeda, Takuya [1 ]
Nagamune, Hideki [1 ]
机构
[1] Univ Tokushima, Fac Engn, Dept Biol Sci & Technol, Tokushima 7708506, Japan
关键词
synthesis; bis-quaternary ammonium compounds; antimicrobial activity;
D O I
10.1016/j.ejmech.2005.10.021
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of new bis-quatemary ammonium compounds (bis-QACs), 4,4'-(2,9-dioxadecane) bis(I-alkylpyridinium bromide)s, 3,3'-(2,9-dioxadecane)bis(1-alkylpyridinium bromide)s and 3,3'-(2,7-dioxaoctane)bis(1-decylpyridinium bromide) was synthesized. The compounds were evaluated by their activities against bacteria, molds and yeasts; the activities were expressed as the minimum inhibitory concentrations (MIC) and/or the minimum bactericidal concentrations (MBC). Compound 4,4'-(2,9-dioxadecane) bis(1-decylpyridinium bromide) had MIC values which exceeded those of benzalkoniumchloride and thiabendazole. It was in vitro active against a broad spectrum of Gram-negative and Gram-positive bacteria, against yeasts and some molds, it had high solubility and thermal decomposition temperature. The relationships between structure and biological activity of the tested bis-QACs are discussed. (c) 2006 Elsevier SAS. All rights reserved.
引用
收藏
页码:437 / 444
页数:8
相关论文
共 50 条
  • [31] Synthesis and Antimicrobial Studies of a New Series of Bis-Heterocycles
    Jayashankara, B.
    Rai, K. M. Lokanatha
    E-JOURNAL OF CHEMISTRY, 2008, 5 (02) : 370 - 376
  • [32] Synthesis and antibacterial activities of water-soluble methacrylate polymers containing quaternary ammonium compounds
    Dizman, Bekir
    Elasri, Mohamed O.
    Mathias, Lon J.
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2006, 44 (20) : 5965 - 5973
  • [33] Synthesis of New Quaternary Ammonium Salts with a Terpene Function and Evaluation of their Fungicidal and Herbicidal Activities
    Zelechowski, Krzysztof
    Gucma, Miroslaw
    Golebiewski, W. Marek
    Krawczyk, Maria
    Michalczyk, Alicja Katarzyna
    ACTA CHIMICA SLOVENICA, 2020, 67 (01) : 325 - 335
  • [34] Synthesis, characterization and antimicrobial activities of new bis-hydrazonothioxothiazolidinone derivatives
    Dixit, Ritu B.
    Bulsara, Ankit P.
    Mehta, Hemal B.
    Dixit, Bharat C.
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2012, 16 (02) : 193 - 197
  • [35] Synthesis and evaluation of antimicrobial activity of a new series of bis(isoxazoline) derivatives
    Jayashankara, B.
    Rai, K. M. Lokanatha
    ARKIVOC, 2008, : 75 - 85
  • [36] Synthesis, Structure, Surface and Antimicrobial Properties of New Oligomeric Quaternary Ammonium Salts with Aromatic Spacers
    Brycki, Bogumil
    Kozirog, Anna
    Kowalczyk, Iwona
    Pospieszny, Tomasz
    Materna, Paulina
    Marciniak, Jedrzej
    MOLECULES, 2017, 22 (11):
  • [37] Synthesis, physicochemical and antimicrobial properties of cardanol-derived quaternary ammonium compounds (QACs) with heterocyclic polar head
    Ma, Jingyi
    Liu, Na
    Huang, Mengen
    Wang, Limin
    Han, Jianwei
    Qian, Hui
    Che, Fei
    JOURNAL OF MOLECULAR LIQUIDS, 2019, 294
  • [38] Antimicrobial Properties of a Biocide Based on Quaternary Ammonium Compounds plus Polyhexamethylene Guanidine and Possible Methods for Its Deactivation
    Yu. V. Litti
    D. V. Serdyukov
    O. V. Kanunnikov
    V. A. Akselrod
    N. G. Loiko
    Applied Biochemistry and Microbiology, 2021, 57 : 962 - 972
  • [39] Antimicrobial Properties of a Biocide Based on Quaternary Ammonium Compounds plus Polyhexamethylene Guanidine and Possible Methods for Its Deactivation
    Litti, Yu. V.
    Serdyukov, D. V.
    Kanunnikov, O. V.
    Akselrod, V. A.
    Loiko, N. G.
    APPLIED BIOCHEMISTRY AND MICROBIOLOGY, 2021, 57 (09) : 962 - 972
  • [40] Phosphorus-nitrogen compounds. part 38. Syntheses, characterizations, cytotoxic, antituberculosis and antimicrobial activities and DNA interactions of spirocyclotetraphosphazenes with bis-ferrocenyl pendant arms
    Elmas, Gamze
    Okumus, Aytug
    Cemaloglu, Resit
    Kilic, Zeynel
    Celik, Suheyla Pinar
    Acik, Leyla
    Tunali, Beste Cagdas
    Turk, Mustafa
    Cerci, Nebahat Aytuna
    Guzel, Remziye
    Hokelek, Tuncer
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 853 : 93 - 106