N-(2-hydroxyethyl)-N,N-dimethyldodecane-1-aminium 4-methylbenzenesulphonate | 55489-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-hydroxyethyl)-N,N-dimethyldodecane-1-aminium 4-methylbenzenesulphonate
• 英文别名: N-(2-hydroxyethyl)-N,N-dimethyl-1-dodecylammonium tosylate；Dodecyl-(2-hydroxyethyl)-dimethylazanium;4-methylbenzenesulfonate
• CAS: 55489-21-9
• 化学式: C₇H₇O₃S*C₁₆H₃₆NO
• 分子量: 429.665
• InChiKey: UCWZIKIKVGIKHD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxyethyl)-N,N-dimethyldodecane-1-aminium 4-methylbenzenesulphonate 、 phosphorodichloridic acid pentyl ester 在 吡啶 、 水 作用下， 反应 1.0h， 生成 2-(N-dodecyl-N,N-dimethylaminio) ethyl pentyl phosphate
  参考文献：
  名称：

  Synthesis of structural analogues of hexadecylphosphocholine and their antineoplastic, antimicrobial and amoebicidal activity

  摘要：

  Twelve derivatives of hexadecylphosphocholine (miltefosine) were synthesized to determine how the position and length of the alkyl chain within the molecule influence their biological activities. The prepared alkylphosphocholines have the same molecular formula as miltefosine. Activity of the compounds was studied against a spectrum of tumour cells, two species of protozoans, bacteria and yeast. Antitumour efficacy of some alkylphosphocholines measured up on MCF-7, A2780, HUT-78 and THP-1 cell lines was higher than that of miltefosine. The compounds showed antiprotozoal activity against Acanthamoeba lugdunensis and Acanthamoeba quina. Some of them also possess fungicidal activity against Candida albicans equal to miltefosine. No antibacterial activity was observed against Staphylococcus aureus and Escherichia coil. A difference in position of a long hydrocarbon chain within the structure with maximum efficacy was observed for antitumour, antiprotozoal and antifungal activity. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.014
• 作为产物：
  描述：

  N,N-二甲基乙醇胺 、 对甲苯磺酸十二酯 以 乙腈 为溶剂， 反应 4.0h， 以73.9%的产率得到N-(2-hydroxyethyl)-N,N-dimethyldodecane-1-aminium 4-methylbenzenesulphonate
  参考文献：
  名称：

  杂环异形表面活性剂的合成、聚集特性及抗原生动物活性

  摘要：

  合成了一系列四种异型表面活性剂：2-癸基[十二烷基(二甲基)氨]乙基磷酸酯、癸基2-(1-十二烷基吡咯烷-1-基)乙基磷酸酯、癸基2-(1-十二烷基哌啶-1-基)磷酸乙酯和2-(1-十二烷基吗啉-1-基)乙基磷酸癸酯。研究了制备的化合物对棘阿米巴 lugdunensis 的抗原生动物活性。Decyl 2-(1-dodecylpyrrolidinio-1-yl)ethyl phosphate 表现出最好的杀菌活性。异质表面活性剂的活性与其聚集特性进行了比较。© 2010 Wiley Periodicals, Inc. 21:203–209, 2010；在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20587

  DOI：

  10.1002/hc.20587

文献信息

• Synthesis and biological activity of dialkylphosphocholines
  作者：Miloš Lukáč、Martin Mrva、Eva Fischer-Fodor、Ivan Lacko、Marián Bukovský、Natalia Miklášová、František Ondriska、Ferdinand Devínsky

  DOI：10.1016/j.bmcl.2009.09.079

  日期：2009.11

  A series of dialkylphosphocholines were prepared and evaluated for their biological activity. The antiprotozoal activity was determined against Acanthamoeba lugdunensis. Compound 15 exhibited excellent trophocidal activity. None of the tested dialkylphosphocholines exhibited better fungicidal activity against Candida albicans than miltefosine. The antineoplastic activity was determined against HeLa. The most cytotoxic was compound 10, which was more active against tumor cells as against normal cells. (C) 2009 Elsevier Ltd. All rights reserved.