all-(E)-13-phenyltrideca-8,10,12-trien-6-yn-1-ol

• 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-8,10,12-trien-6-yn-1-ol
• 英文别名: (8E,10E,12E)-13-phenyltrideca-8,10,12-trien-6-yn-1-ol
• 化学式: C₁₉H₂₂O
• 分子量: 266.383
• InChiKey: BTWVOJAAMLAOHV-BLJGMQTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  7
• 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-8,10,12-trien-6-yn-1-ol 、 2-氯-2-氧-1,3,2-二氧磷杂环戊烷 在 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 生成
  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+