hexadecyl [2-(N-methylmorpholinio)ethyl]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: hexadecyl [2-(N-methylmorpholinio)ethyl]phosphate
• 英文别名: D-20681；(N-methylmorpholino)ethanol hexadecyl phosphonate；hexadecyl 2-(4-methylmorpholin-4-ium-4-yl)ethyl phosphate
• 化学式: C₂₃H₄₈NO₅P
• 分子量: 449.612
• InChiKey: DKIZRNDMUNKRJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-十六烷醇 、 S4-(2-hydroxyethyl)-4-methylmorpholin-4-ium 4-methylbenzenesulfonate 在 三乙胺 、 三氯氧磷 、 吡啶 、 水 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以10.8%的产率得到hexadecyl [2-(N-methylmorpholinio)ethyl]phosphate
  参考文献：
  名称：

  十六烷基磷酸胆碱和十六烷基三甲基溴化铵的二烷基氨基和氮杂环类似物：磷酸根基团和铵阳离子环境对其生物学活性的影响

  摘要：

  已经合成了十六烷基磷胆碱和十六烷基三甲基溴化铵的一系列二烷基氨基和氮杂环类似物。制备的化合物显示出显着的细胞毒性，抗真菌和抗原生动物活性。与季铵化合物相比，烷基磷酸胆碱对白色念珠菌具有更高的抗真菌活性。然而，与烷基磷酸胆碱相比，季铵化合物对人肿瘤细胞和卢氏棘阿米巴具有显着更高的活性。另外，已经研究了它们的溶血毒性。讨论了被测化合物的结构与生物学活性之间的关系。

  DOI：

  10.1016/j.ejmech.2009.08.011

文献信息

• Alkyl and Alkoxyethyl Antineoplastic Phospholipids
  作者：Maria Koufaki、Vanessa Polychroniou、Theodora Calogeropoulou、Andrew Tsotinis、Markus Drees、Heiner H. Fiebig、Sophie LeClerc、Hans R. Hendriks、Alexandros Makriyannis

  DOI：10.1021/jm9509152

  日期：1996.1.1

  Two series of phosphodiester ether lipid analogs with (N-methylmorpholino)ethyl or (N-methylpiperidino)ethyl polar head groups and long aliphatic or alkoxyethyl chains in the nonpolar portion of the molecule were synthesized as potential antineoplastic agents. The cytotoxic activity of these compounds (9-19) was evaluated in vitro against a panel of six human tumor xenografts and in two biochemical, mechanism-based screens (cdc2 kinase and cdc25 phosphatase). Analogs 13, 14, 17, and 19 showed activity in the in vitro tests. Specifically, 14 and 17 were more active than the reference compound hexadecylphosphocholine (Miltefosine, He-PC) while 13 and 19 possessed activity similar to that of the control. Of the analogs tested the one with the highest potency and least toxicity (17) has an N-methylpiperidino head group and a C-16 alkyl chain. In the mechanism-based tests 11 showed weak inhibitory activity in the cdc25 phosphatase screen.
• Dialkylamino and nitrogen heterocyclic analogues of hexadecylphosphocholine and cetyltrimetylammonium bromide: Effect of phosphate group and environment of the ammonium cation on their biological activity
  作者：Miloš Lukáč、Ján Mojžiš、Gabriela Mojžišová、Martin Mrva、František Ondriska、Jindra Valentová、Ivan Lacko、Marián Bukovský、Ferdinand Devínsky、Janka Karlovská

  DOI：10.1016/j.ejmech.2009.08.011

  日期：2009.12

  dialkylamino and nitrogen heterocyclic analogues of hexadecylphosphocholine and cetyltrimethylammonium bromide have been synthesized. The prepared compounds exhibit significant cytotoxic, antifungal and antiprotozoal activities. Alkylphosphocholines possess higher antifungal activity against Candida albicans in comparison with quaternary ammonium compounds. However, quaternary ammonium compounds exhibit

  已经合成了十六烷基磷胆碱和十六烷基三甲基溴化铵的一系列二烷基氨基和氮杂环类似物。制备的化合物显示出显着的细胞毒性，抗真菌和抗原生动物活性。与季铵化合物相比，烷基磷酸胆碱对白色念珠菌具有更高的抗真菌活性。然而，与烷基磷酸胆碱相比，季铵化合物对人肿瘤细胞和卢氏棘阿米巴具有显着更高的活性。另外，已经研究了它们的溶血毒性。讨论了被测化合物的结构与生物学活性之间的关系。