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
  • [1] The antimicrobial activities of a series of bis-quaternary ammonium compounds
    Xu Zhuo Sun~(a
    Chinese Chemical Letters, 2011, 22 (08) : 887 - 890
  • [2] The antimicrobial activities of a series of bis-quaternary ammonium compounds
    Sun, Xu Zhuo
    Wang, Ning
    Cao, Di
    Hu, Zi Yu
    Mao, Pu
    Zhang, Hai Bo
    Zhou, Xiao Hai
    CHINESE CHEMICAL LETTERS, 2011, 22 (08) : 887 - 890
  • [3] EVALUATION OF THE ANTIMICROBIAL EFFECTS OF NEW HETEROCYCLIC BIS-QUATERNARY AMMONIUM COMPOUNDS ON BIOFILMS
    Constantin, Oana E.
    Furdui, Bianca
    Bahrim, Gabriela
    Dinica, Rodica M.
    SCIENTIFIC STUDY AND RESEARCH-CHEMISTRY AND CHEMICAL ENGINEERING BIOTECHNOLOGY FOOD INDUSTRY, 2016, 17 (02): : 199 - 210
  • [4] Evaluation of the antimicrobial effects of new heterocyclic bis-quaternary ammonium compounds on biofilms
    Furdui, Bianca (bfurdui@ugal.ro), 2016, ALMA MATER Publishing House âÇô VASILE ALECSANDRI UNIVERSITY OF BACAU (17):
  • [5] UNSATURATED BIS-QUATERNARY AMMONIUM COMPOUNDS
    KOST, TA
    FREIDLIN.RK
    IZVESTIYA AKADEMII NAUK SSSR-SERIYA KHIMICHESKAYA, 1970, (09): : 2124 - &
  • [6] ESTIMATION OF BIS-QUATERNARY AMMONIUM COMPOUNDS
    CAMPBELL, H
    MUGGLETON, DF
    CHEMISTRY & INDUSTRY, 1952, (51) : 1244 - 1244
  • [7] Synthesis and antimicrobial activities of new water-soluble bis-quaternary ammonium methacrylate polymers
    Dizman, B
    Elasri, MO
    Mathias, LJ
    JOURNAL OF APPLIED POLYMER SCIENCE, 2004, 94 (02) : 635 - 642
  • [8] THE PHARMACOLOGY OF SOME BIS-QUATERNARY AMMONIUM COMPOUNDS
    HOROVITZ, ZP
    REIF, EC
    BUCKLEY, JP
    JOURNAL OF THE AMERICAN PHARMACEUTICAL ASSOCIATION, 1958, 47 (10): : 718 - 721
  • [9] Antimicrobial, Antimalarial, and Antileishmanial Activities of Mono- and Bis-quaternary Pyridinium Compounds
    Bharate, Sandip B.
    Thompson, Charles M.
    CHEMICAL BIOLOGY & DRUG DESIGN, 2010, 76 (06) : 546 - 551
  • [10] ANTICHOLINESTERASE ACTIVITIES OF SOME BIS-QUATERNARY AMMONIUM SALTS
    CAVALLITO, CJ
    SANDY, P
    BIOCHEMICAL PHARMACOLOGY, 1959, 2 (04) : 233 - 242