N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-2',2'-difluoro-3-acetylcytidine | 608122-31-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-2',2'-difluoro-3-acetylcytidine
• 英文别名: [(2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,4-difluorooxolan-3-yl] acetate
• CAS: 608122-31-2
• 化学式: C₂₄H₃₁F₂N₃O₆Si
• 分子量: 523.609
• InChiKey: ZLEFLQFBIFEFEJ-YFVAEKQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-2',2'-difluoro-3-acetylcytidine 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以72%的产率得到N-benzoyl-2'-deoxy-2',2'-difluoro-3-acetylcytidine
  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：

  吉西他滨 在 吡啶 、 咪唑 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 N-benzoyl-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-2',2'-difluoro-3-acetylcytidine
  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