5-bromo-ara-L-cytidine | 415704-82-4

• 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: 5-bromo-ara-L-cytidine
• CAS: 415704-82-4
• 化学式: C₉H₁₂BrN₃O₅
• 分子量: 322.115
• InChiKey: HRDXGYQCVPZEJE-FEEAIGFJSA-N

物化性质

• 熔点：
  207-210 °C
• 沸点：
  555.4±60.0 °C(Predicted)
• 密度：
  2.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  130.83
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  (2S,3R,4S,5S)-2-(4-amino-5-bromo-2-oxopyrimidin-1(2H)-yl)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate 在 甲醇 、 sodium methylate 作用下， 反应 4.0h， 以91%的产率得到5-bromo-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