2-(N-decyl-N,N-dimethylaminio) ethyl heptyl phosphate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 2-(N-decyl-N,N-dimethylaminio) ethyl heptyl phosphate
• 英文别名: 2-[Decyl(dimethyl)azaniumyl]ethyl heptyl phosphate；2-[decyl(dimethyl)azaniumyl]ethyl heptyl phosphate
• 化学式: C₂₁H₄₆NO₄P
• 分子量: 407.574
• InChiKey: NPJCUXYPCHQLRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  27
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  正庚醇 在 吡啶 、 三乙胺 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 2-(N-decyl-N,N-dimethylaminio) ethyl heptyl 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

文献信息

• A Combinatorially-Derived Structural Phase Diagram for 42 Zwitterionic Geminis
  作者：Fredric M. Menger、Andrey V. Peresypkin

  DOI：10.1021/ja003779l

  日期：2001.6.1
• Synthesis of structural analogues of hexadecylphosphocholine and their antineoplastic, antimicrobial and amoebicidal activity
  作者：Lukáš Timko、Eva Fischer-Fodor、Mária Garajová、Martin Mrva、Gabriela Chereches、František Ondriska、Marián Bukovský、Miloš Lukáč、Janka Karlovská、Janka Kubincová、Ferdinand Devínsky

  DOI：10.1016/j.ejmech.2015.02.014

  日期：2015.3

  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.