trans-(2-hydroxycyclohexyl)-N,N,N-trimethylammonium toluene-4-sulfonate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-(2-hydroxycyclohexyl)-N,N,N-trimethylammonium toluene-4-sulfonate
• 英文别名: [(1R,2R)-2-hydroxycyclohexyl]-trimethylazanium;4-methylbenzenesulfonate
• 化学式: C₇H₇O₃S*C₉H₂₀NO
• 分子量: 329.461
• InChiKey: FQDOPWAJIXUGNO-VTLYIQCISA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  1-十六烷醇 、 trans-(2-hydroxycyclohexyl)-N,N,N-trimethylammonium toluene-4-sulfonate 在 三乙胺 、 三氯氧磷 、 吡啶 、 水 作用下， 以 四氢呋喃 、 氯仿 、 异丙醇 为溶剂， 反应 50.5h， 以50%的产率得到trans-{2-[(hexadecyloxy)hydroxyphosphinyloxy]}-N,N,N-trimethylcyclohexaneammonium inner salt
  参考文献：
  名称：

  Design and Synthesis of Potent Antileishmanial Cycloalkylidene-Substituted Ether Phospholipid Derivatives

  摘要：

  Two series of novel ether phospholipids (EPs) have been synthesized. The first includes cyclodecylideneor cyclopentadecylidene-substituted EPs carrying N,N,N-trimethylammonium or N-methylpiperidino or N-methylmorpholino head groups. The second series encompasses more rigid head groups in combination with cycloalkylidene moieties in the lipid portion. In addition, hydrogenated derivatives were obtained. All the new analogues, except 33, were 1.5- to 62-fold more potent than miltefosine against the intracellular L. infantum, and the most active ones were also less cytotoxic against the human monocytic cell line THP1 and less hemolytic than miltefosine. The analogues that combine high potency with low cytotoxicity and hemolytic activity were 19, 37, 2123, 38, 39, and 40. Cyclopentadecylpentylphosphocholine (38) possesses an IC50 of 0.7 mu M against L. infantum amastigotes and is the least cytotoxic analogue, since it does not present toxicity against THP1 macrophages, even at a concentration that is 800-fold the antiparasitic IC50 value, and does not present significant hemolytic activity.

  DOI：

  10.1021/jm701166b
• 作为产物：
  描述：

  trans-2-(N,N-dimethylamino)cyclohexanol 、 对甲苯磺酸甲酯 以 乙醚 为溶剂， 反应 48.0h， 以85%的产率得到trans-(2-hydroxycyclohexyl)-N,N,N-trimethylammonium toluene-4-sulfonate
  参考文献：
  名称：

  Design and Synthesis of Potent Antileishmanial Cycloalkylidene-Substituted Ether Phospholipid Derivatives

  摘要：

  Two series of novel ether phospholipids (EPs) have been synthesized. The first includes cyclodecylideneor cyclopentadecylidene-substituted EPs carrying N,N,N-trimethylammonium or N-methylpiperidino or N-methylmorpholino head groups. The second series encompasses more rigid head groups in combination with cycloalkylidene moieties in the lipid portion. In addition, hydrogenated derivatives were obtained. All the new analogues, except 33, were 1.5- to 62-fold more potent than miltefosine against the intracellular L. infantum, and the most active ones were also less cytotoxic against the human monocytic cell line THP1 and less hemolytic than miltefosine. The analogues that combine high potency with low cytotoxicity and hemolytic activity were 19, 37, 2123, 38, 39, and 40. Cyclopentadecylpentylphosphocholine (38) possesses an IC50 of 0.7 mu M against L. infantum amastigotes and is the least cytotoxic analogue, since it does not present toxicity against THP1 macrophages, even at a concentration that is 800-fold the antiparasitic IC50 value, and does not present significant hemolytic activity.

  DOI：

  10.1021/jm701166b

文献信息

• Design and Synthesis of Potent Antileishmanial Cycloalkylidene-Substituted Ether Phospholipid Derivatives
  作者：Theodora Calogeropoulou、Panagiotis Angelou、Anastasia Detsi、Irene Fragiadaki、Effie Scoulica

  DOI：10.1021/jm701166b

  日期：2008.2.1

  Two series of novel ether phospholipids (EPs) have been synthesized. The first includes cyclodecylideneor cyclopentadecylidene-substituted EPs carrying N,N,N-trimethylammonium or N-methylpiperidino or N-methylmorpholino head groups. The second series encompasses more rigid head groups in combination with cycloalkylidene moieties in the lipid portion. In addition, hydrogenated derivatives were obtained. All the new analogues, except 33, were 1.5- to 62-fold more potent than miltefosine against the intracellular L. infantum, and the most active ones were also less cytotoxic against the human monocytic cell line THP1 and less hemolytic than miltefosine. The analogues that combine high potency with low cytotoxicity and hemolytic activity were 19, 37, 2123, 38, 39, and 40. Cyclopentadecylpentylphosphocholine (38) possesses an IC50 of 0.7 mu M against L. infantum amastigotes and is the least cytotoxic analogue, since it does not present toxicity against THP1 macrophages, even at a concentration that is 800-fold the antiparasitic IC50 value, and does not present significant hemolytic activity.