Synthesis and antimicrobial properties of imidazolium and pyrrolidinonium salts
Synthesis and antimicrobial properties of imidazolium and pyrrolidinonium salts
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DOI：
10.1016/j.bmc.2004.01.003
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发表时间：
2004-03-01
影响因子：
3.5
通讯作者：
Yoo, ID
中科院分区：
文献类型：
--
作者：
Demberelnyamba, D;Kim, KS;Yoo, ID
为了开发新的消毒剂和防腐剂，我们寻找对革兰氏阳性菌、革兰氏阴性菌和真菌具有高杀菌活性的化合物。合成了三个不同系列的季咪唑鎓和吡咯烷鎓盐：系列A（1-烷基-3-甲基咪唑鎓氯化物和溴化物）;系列B（1-烷基-2-甲基-3-羟乙基咪唑鎓氯化物）;和系列C（N-烷基-N-羟乙基吡咯烷鎓）。系列B和C是新设计的。这三个系列进行了测试，以评估其抗菌和抗真菌性能的第一次。研究中使用了7种微生物菌株：大肠杆菌KCTC 1924、鼠伤寒沙门氏菌KCTC 1926、金黄色葡萄球菌209 KCTC 1916、金黄色葡萄球菌R209 KCTC 1928、枯草芽孢杆菌KCTC 1914、白色念珠菌KCTC 1940和规则小球藻。通过细菌和真菌生长抑制来测量抗微生物效率，表示为最小抑菌浓度（MIC）值。系列A和B咪唑盐对所检测的革兰氏阴性菌、革兰氏阳性菌和真菌具有非常好的抗微生物活性。还发现吡咯烷鎓盐对一些测试的微生物具有低MIC。盐的抗细菌和抗真菌活性特性取决于咪唑鎓和吡咯烷鎓环中官能团的结构和烷基链的长度。在合成的季铵咪唑鎓盐和吡咯烷鎓盐中，含有长烷基链并在咪唑鎓环结构中引入羟乙基链和甲基的咪唑鎓盐导致广谱活性抗微生物剂，其不仅具有抑菌性质，而且可以是强有力的杀菌剂。(C)2004爱思唯尔有限公司保留所有权利。
For the purpose of developing new disinfectants and antiseptics, we searched for compounds having high bactericidal activity against gram-positive bacteria, gram-negative bacteria, and fungi. Three different series of quaternary imidazolium and pyrrolidinonium, salts were synthesized: series A (1-alkyl-3-methylimidazolium chlorides and bromides); series B (1-alkyl-2-methyl-3-hydroxyethylimidazolium chlorides); and series C (N-alkyl-N-hydroxyethylpyrrolidinonium). Series B and C were newly designed. These three series were tested to evaluate their antibacterial and antifungal properties for the first time. Seven microbial strains were used in the study: Escherichia coli KCTC1924, Salmonella typhimurium KCTC1926, Staphylococcus aureus 209 KCTC1916, Staphylococcus aureus R209 KCTC1928, Bacillus subtilis KCTC1914, Candida albicans KCTC1940, and Chlorella regularis. The antimicrobial efficiency was measured by bacterial and fungal growth inhibition expressed as minimal inhibitory concentration (MIC) values. Series A and B imidazolium salts had very good antimicrobial activity against the examined Gram-negative bacteria, Gram-positive bacteria, and fungi. Also the pyrrolidinonium salt was found to have low MIC for some of tested microorganisms. The antibacterial and antifungal active properties of the salts depend upon the structure of functional groups and the alkyl chain length in the imidazolium and pyrrolidinonium ring. Among the synthesized quaternary imidazolium and pyrrolidinonium salts, the imidazolium salts containing a long alkyl chain and the introduction of a hydroxyethyl chain and methyl group into the imidazolium ring structure leads to broad spectrum active antimicrobial agents which not only have bacteriostatic properties but could be powerful bactericides. (C) 2004 Elsevier Ltd. All rights reserved.