N-benzoyl-1-(2',3'-di-O-acetyl-β-D-arabinofuranosyl-5'-monophosphate-1-dodecylthio-2-decyloxypropyl)cytidine | 608122-28-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: N-benzoyl-1-(2',3'-di-O-acetyl-β-D-arabinofuranosyl-5'-monophosphate-1-dodecylthio-2-decyloxypropyl)cytidine
• CAS: 608122-28-7
• 化学式: C₄₅H₇₂N₃O₁₂PS
• 分子量: 910.119
• InChiKey: CCYSRVVCMUBNJD-KEOLZMNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.57
• 重原子数：
  62.0
• 可旋转键数：
  34.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  190.81
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  N-benzoyl-1-(2',3'-di-O-acetyl-β-D-arabinofuranosyl-5'-monophosphate-1-dodecylthio-2-decyloxypropyl)cytidine 在 甲醇 、 氨 作用下， 反应 24.0h， 以81%的产率得到(β-D-arabinofuranosyl-5'-monophosphate-1-dodecylthio-2-decyloxypropyl)cytidine
  参考文献：
  名称：

  Synthesis and Cytotoxic Activity of Two Novel 1-Dodecylthio-2-decyloxypropyl-3-phosphatidic Acid Conjugates with Gemcitabine and Cytosine Arabinoside

  摘要：

  Cytosine arabinoside (ara-C) and gemcitabine (dFdC) are two standard chemotherapy drugs used in the treatment of patients with various cancers. To alter the pharmacokinetic and pharmacodynamic properties of these molecules, we conjugated a synthetic phospholipid to both ara-C and dFdC and investigated their chemotherapeutic potential. The dFdC conjugate had greater cytotoxic activity compared with the ara-C conjugate and demonstrated notable cytotoxicity against all human cell lines tested.

  DOI：

  10.1021/jm020571x
• 作为产物：
  描述：

  阿糖胞苷 在 吡啶 、 咪唑 、 2,4,6-三异丙基苯磺酰氯 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 126.0h， 生成 N-benzoyl-1-(2',3'-di-O-acetyl-β-D-arabinofuranosyl-5'-monophosphate-1-dodecylthio-2-decyloxypropyl)cytidine
  参考文献：
  名称：

  Synthesis and Cytotoxic Activity of Two Novel 1-Dodecylthio-2-decyloxypropyl-3-phosphatidic Acid Conjugates with Gemcitabine and Cytosine Arabinoside

  摘要：

  Cytosine arabinoside (ara-C) and gemcitabine (dFdC) are two standard chemotherapy drugs used in the treatment of patients with various cancers. To alter the pharmacokinetic and pharmacodynamic properties of these molecules, we conjugated a synthetic phospholipid to both ara-C and dFdC and investigated their chemotherapeutic potential. The dFdC conjugate had greater cytotoxic activity compared with the ara-C conjugate and demonstrated notable cytotoxicity against all human cell lines tested.

  DOI：

  10.1021/jm020571x