2',3',5'-tri-O-benzoyl-ara-L-cytidine | 1382804-49-0

• 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: 2',3',5'-tri-O-benzoyl-ara-L-cytidine
• CAS: 1382804-49-0
• 化学式: C₃₀H₂₅N₃O₈
• 分子量: 555.544
• InChiKey: LNTGQFREGXHRAN-MNPUUQGPSA-N

物化性质

• 沸点：
  717.8±70.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  149.04
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-benzoyl-ara-L-cytidine 在 甲醇 、 sodium methylate 作用下， 反应 4.0h， 以86%的产率得到阿扎胞苷杂质20
  参考文献：
  名称：

  Synthesis and Cytotoxic Activity of Novel 5-Substituted-1-(β-L-Arabinofuranosyl) Pyrimidine Nucleosides

  摘要：

  A series of new 5-halogeno-1-(beta-L-arabinofuranosyl)uracils and their cytosine analogues were synthesized by halogenation of ara-L-uridine and ara-L-cytidine, respectively. The 5-(2-thienyl) and 5-halogenothienyl derivatives of both series were also prepared in excellent yields by Stille coupling followed by halogenation. All of these syntheses were based on benzoyl-protected derivatives. In vitro cytotoxicity experiments carried out using L1210 mouse leukemia cells showed that 5-(2-thienyl)-ara-L-uridine was the most potent compound of the new compounds; the majority of the analogues were not effective up to 200 mu M concentrations.

  DOI：

  10.1080/15257770.2012.689410
• 作为产物：
  描述：

  1-(β-L-arabinofuranosyl)uracil 在 吡啶 、 1H-1,2,4-三唑 、 三氯氧磷 作用下， 反应 32.0h， 生成 2',3',5'-tri-O-benzoyl-ara-L-cytidine
  参考文献：
  名称：

  Synthesis and Cytotoxic Activity of Novel 5-Substituted-1-(β-L-Arabinofuranosyl) Pyrimidine Nucleosides

  摘要：

  A series of new 5-halogeno-1-(beta-L-arabinofuranosyl)uracils and their cytosine analogues were synthesized by halogenation of ara-L-uridine and ara-L-cytidine, respectively. The 5-(2-thienyl) and 5-halogenothienyl derivatives of both series were also prepared in excellent yields by Stille coupling followed by halogenation. All of these syntheses were based on benzoyl-protected derivatives. In vitro cytotoxicity experiments carried out using L1210 mouse leukemia cells showed that 5-(2-thienyl)-ara-L-uridine was the most potent compound of the new compounds; the majority of the analogues were not effective up to 200 mu M concentrations.

  DOI：

  10.1080/15257770.2012.689410

文献信息

• Synthesis and Cytotoxic Activity of Novel 5-Substituted-1-(β-L-Arabinofuranosyl) Pyrimidine Nucleosides
  作者：Róbert Sendula、Erika Orbán、Ferenc Hudecz、Gyula Sági、István Jablonkai

  DOI：10.1080/15257770.2012.689410

  日期：2012.6

  A series of new 5-halogeno-1-(beta-L-arabinofuranosyl)uracils and their cytosine analogues were synthesized by halogenation of ara-L-uridine and ara-L-cytidine, respectively. The 5-(2-thienyl) and 5-halogenothienyl derivatives of both series were also prepared in excellent yields by Stille coupling followed by halogenation. All of these syntheses were based on benzoyl-protected derivatives. In vitro cytotoxicity experiments carried out using L1210 mouse leukemia cells showed that 5-(2-thienyl)-ara-L-uridine was the most potent compound of the new compounds; the majority of the analogues were not effective up to 200 mu M concentrations.