Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-5-(hexadecyloxy-hydroxy-phosphoryloxymethyl)-tetrahydro-furan-3-yl ester | 203182-46-1

• 英文名称: Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-5-(hexadecyloxy-hydroxy-phosphoryloxymethyl)-tetrahydro-furan-3-yl ester
• CAS: 203182-46-1
• 化学式: C₃₁H₅₂N₃O₁₁P
• 分子量: 673.741
• InChiKey: MAIRAGUYBCBWRS-PYYPWFDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  46.0
• 可旋转键数：
  23.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  181.58
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-5-(hexadecyloxy-hydroxy-phosphoryloxymethyl)-tetrahydro-furan-3-yl ester 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hexadecyl hydrogen phosphate
  参考文献：
  名称：

  Synthesis and cytostatical evaluation of cytidine- and adenosine-5′-hexadecylphosphate and their phosphonate analogs

  摘要：

  Four phospholipid conjugates containing the non-cytotoxic nucleosides cytidine and adenosine were prepared by condensation reactions, and their cytotoxic activity was tested in vitro against the human immortalized mammary epithelial cell H184 A(1)N(4), the human mammary tumor cells MaTu and MCF7 and the B lymphoblast cell line Daudi. The synthesized compounds showed considerable activity towards H184 A(1)N(4), MaTu and Daudi cells, but they were not effective against MCF7 cells. The phosphorus moiety-either monophosphate or monophosphonate-does not influence the effectiveness of the phospholipid derivatives in the case of the solid tumor cell lines and H184 A(1)N(4). The leukemic Daudi cell line is strongly sensitive towards the different types of ester as well as to the type of the nucleoside component. Adenosine-5'-hexadecylphosphate proved to be the most potent compound among the substances prepared (IC50: 9.0 mu mol). (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00074-1
• 作为产物：
  描述：

  5'-胞苷酸 在 吡啶 、 2,4,6-三异丙基苯磺酰氯 作用下， 反应 16.0h， 生成 Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-5-(hexadecyloxy-hydroxy-phosphoryloxymethyl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis and cytostatical evaluation of cytidine- and adenosine-5′-hexadecylphosphate and their phosphonate analogs

  摘要：

  Four phospholipid conjugates containing the non-cytotoxic nucleosides cytidine and adenosine were prepared by condensation reactions, and their cytotoxic activity was tested in vitro against the human immortalized mammary epithelial cell H184 A(1)N(4), the human mammary tumor cells MaTu and MCF7 and the B lymphoblast cell line Daudi. The synthesized compounds showed considerable activity towards H184 A(1)N(4), MaTu and Daudi cells, but they were not effective against MCF7 cells. The phosphorus moiety-either monophosphate or monophosphonate-does not influence the effectiveness of the phospholipid derivatives in the case of the solid tumor cell lines and H184 A(1)N(4). The leukemic Daudi cell line is strongly sensitive towards the different types of ester as well as to the type of the nucleoside component. Adenosine-5'-hexadecylphosphate proved to be the most potent compound among the substances prepared (IC50: 9.0 mu mol). (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00074-1