Phosphoric acid (3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester hexadecyl ester | 203182-52-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: Phosphoric acid (3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester hexadecyl ester
• CAS: 203182-52-9
• 化学式: C₂₉H₅₀N₅O₇P
• 分子量: 611.719
• InChiKey: KXNLGQPCIDWARW-ZYWWQZICSA-N

物化性质

• 沸点：
  733.481±70.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.340±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  42.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  153.07
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Phosphoric acid (3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester hexadecyl ester 在 溶剂黄146 作用下， 反应 2.0h， 以51%的产率得到adenosine 5'-hexadecylphosphate
  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：

  腺苷 在 吡啶 、 2,4,6-三异丙基苯磺酰氯 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 18.5h， 生成 Phosphoric acid (3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester hexadecyl 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