all-(E)-13-phenyltrideca-6,8,10,12-tetraen-1-ol | 944394-97-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: all-(E)-13-phenyltrideca-6,8,10,12-tetraen-1-ol
• 英文别名: (6E,8E,10E,12E)-13-phenyltrideca-6,8,10,12-tetraen-1-ol
• CAS: 944394-97-2
• 化学式: C₁₉H₂₄O
• 分子量: 268.399
• InChiKey: LTDCYHGYBSKSHI-ZQZHLYLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  all-(E)-13-phenyltrideca-6,8,10,12-tetraen-1-ol 、 2-氯-2-氧-1,3,2-二氧磷杂环戊烷 、 三甲胺 以 乙腈 为溶剂， 反应 3.0h， 以36%的产率得到[(6E,8E,10E,12E)-13-phenyltrideca-6,8,10,12-tetraenyl] 2-(trimethylazaniumyl)ethyl phosphate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Fluorescent Leishmanicidal Analogues of Hexadecylphosphocholine (Miltefosine) as Probes of Antiparasite Mechanisms

  摘要：

  The leishmanicidal mechanism of miltefosine (hexadecylphosphocholine, MT) is not clearly understood. Valuable insights into its mode of action could be obtained by fluorescence techniques, given suitably emitting analogues. In this regard, the synthesis and biological characterization of two fully competent NIT fluorescent analogues is reported here: all-(E)-13-phenyltrideca-6,8,10,12-tetraenylphosphocholine (PTE-MT) and all(E)-13-phenyltrideca-8,10,12-trien-6-ynylphosphocholine (PTRI-MT). Both compounds show large absorption coefficients and a,modest, but usable, fluorescence yield. Their activities were very similar to that of NIT and were recognized by the NIT uptake system of Leishmania. Their localization in living L. donovani promastigotes by confocal microscopy show a homogeneous intracellular distribution of the fluorescence. The concentration of PTRI-MT within the parasites (ca. 1.7 mM) showed a 100-fold enrichment relative to its external concentration. These results are consistent with a multiple target leishmanicidal mechanism for NIT and validate the application of these analogues for pharmacokinetic and diagnostic studies concerning the chemotherapy of leishmaniasis.

  DOI：

  10.1021/jm070595+
• 作为产物：
  描述：

  (2E, 4E)-5-phenylpenta-2,4-dienal 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 copper diacetate 、 碘 、 silver nitrate 、 二乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 27.25h， 生成 all-(E)-13-phenyltrideca-6,8,10,12-tetraen-1-ol
  参考文献：
  名称：

  具有线性共轭多烯和苯基多烯荧光基团的两亲脂质的合成和光谱性质

  摘要：

  这项工作得到了西班牙教育部长 (MEC)（项目 BQU2000-1500 和 BQU2003/04413）的支持。EQ、JD 和 VH 承认来自同一来源的博士前资助。

  DOI：

  10.1002/ejoc.200600954

文献信息

• Synthesis and Spectral Properties of Amphiphilic Lipids with Linear Conjugated Polyene and Phenylpolyene Fluorescent Groups
  作者：Ernesto Quesada、Javier Delgado、Valentín Hornillos、A. Ulises Acuña、Francisco Amat-Guerri

  DOI：10.1002/ejoc.200600954

  日期：2007.5

  This work was supported by the Spanish Ministerio de Educacion y Ciencia (MEC) (Projects BQU2000-1500 and BQU2003/04413). E. Q., J. D. and V. H. acknowledge predoctoral grants from the same source.

  这项工作得到了西班牙教育部长 (MEC)（项目 BQU2000-1500 和 BQU2003/04413）的支持。EQ、JD 和 VH 承认来自同一来源的博士前资助。
• Synthesis and Biological Evaluation of Fluorescent Leishmanicidal Analogues of Hexadecylphosphocholine (Miltefosine) as Probes of Antiparasite Mechanisms
  作者：José M. Saugar、Javier Delgado、Valentín Hornillos、Juan R. Luque-Ortega、Francisco Amat-Guerri、A. Ulises Acuña、Luis Rivas

  DOI：10.1021/jm070595+

  日期：2007.11.1

  The leishmanicidal mechanism of miltefosine (hexadecylphosphocholine, MT) is not clearly understood. Valuable insights into its mode of action could be obtained by fluorescence techniques, given suitably emitting analogues. In this regard, the synthesis and biological characterization of two fully competent NIT fluorescent analogues is reported here: all-(E)-13-phenyltrideca-6,8,10,12-tetraenylphosphocholine (PTE-MT) and all(E)-13-phenyltrideca-8,10,12-trien-6-ynylphosphocholine (PTRI-MT). Both compounds show large absorption coefficients and a,modest, but usable, fluorescence yield. Their activities were very similar to that of NIT and were recognized by the NIT uptake system of Leishmania. Their localization in living L. donovani promastigotes by confocal microscopy show a homogeneous intracellular distribution of the fluorescence. The concentration of PTRI-MT within the parasites (ca. 1.7 mM) showed a 100-fold enrichment relative to its external concentration. These results are consistent with a multiple target leishmanicidal mechanism for NIT and validate the application of these analogues for pharmacokinetic and diagnostic studies concerning the chemotherapy of leishmaniasis.