(E)-3',5'-di-O-acetyl-5-(1,2-dibromovinyl)-2'-deoxyuridine | 866837-08-3

• 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: (E)-3',5'-di-O-acetyl-5-(1,2-dibromovinyl)-2'-deoxyuridine
• 英文别名: 3',5'-di-O-acetyl-5-(1,2-dibromovinyl)-2'-deoxyuridine
• CAS: 866837-08-3
• 化学式: C₁₅H₁₆Br₂N₂O₇
• 分子量: 496.109
• InChiKey: UDZHDKZAGIGFMC-JLAYVEJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  116.69
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (E)-3',5'-di-O-acetyl-5-(1,2-dibromovinyl)-2'-deoxyuridine 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以85%的产率得到(E)-5-(1,2-dibromovinyl)-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis of 5-haloethynyl- and 5-(1,2-dihalo)vinyluracil nucleosides: Antiviral activity and cellular toxicity

  摘要：

  In this article, we report the synthesis of hitherto unknown 5-haloethynyl and 5-(1,2-dihalo)vinyluracil nucleosides in the 2'-deoxy, 3'-deoxy- and ribosyl series, and we discuss their in vitro anti-HIV and anti-HCV activities and cellular toxicitites. As a result, on the basis of their selectivity index (SI) obtained with the HCV replicon system, but also on their cytotoxicity on peripheral blood mononuclear, CEM and VERO cell lines, the best compounds were the 5-bromoethynyluridine (SI = 3.2) and the 5-(1-chloro-2-iodo)vinyluridine (SI > 2.8). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.021
• 作为产物：
  描述：

  5-ethynyl-2'-deoxyuridine 在 溴 作用下， 以 乙腈 为溶剂， 以97%的产率得到(E)-3',5'-di-O-acetyl-5-(1,2-dibromovinyl)-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis of 5-haloethynyl- and 5-(1,2-dihalo)vinyluracil nucleosides: Antiviral activity and cellular toxicity

  摘要：

  In this article, we report the synthesis of hitherto unknown 5-haloethynyl and 5-(1,2-dihalo)vinyluracil nucleosides in the 2'-deoxy, 3'-deoxy- and ribosyl series, and we discuss their in vitro anti-HIV and anti-HCV activities and cellular toxicitites. As a result, on the basis of their selectivity index (SI) obtained with the HCV replicon system, but also on their cytotoxicity on peripheral blood mononuclear, CEM and VERO cell lines, the best compounds were the 5-bromoethynyluridine (SI = 3.2) and the 5-(1-chloro-2-iodo)vinyluridine (SI > 2.8). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.021