| 1146697-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• CAS: 1146697-64-4
• 化学式: C₁₅H₁₈N₂O₈Se
• 分子量: 433.277
• InChiKey: QJYYQJYPKOQXGO-RUZUBIRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.03
• 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：
  0.53
• 拓扑面积：
  133.76
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  在 1H-1,2,4-三唑 、 三氯氧磷 、 ammonium hydroxide 、 氨 作用下， 以 乙腈 、 1,4-二氧六环 、 水 、 甲醇 为溶剂， 反应 4.0h， 以36 mg的产率得到(-)-1-(4-seleno-D-arabinofuranosyl)cytosine
  参考文献：
  名称：

  Discovery of a New Template for Anticancer Agents: 2′-deoxy-2′-fluoro-4′-selenoarabinofuranosyl-cytosine (2′-F-4′-Seleno-ara-C)

  摘要：

  The first synthesis of 2'-deoxy-2'-fluoro-4'-selenoarabinofuranosyl pyrimidines as potent anticancer agents was accomplished using the DAST fluorination as a key step. It was first revealed that selenium atom participated in the DAST fluorination of 4'-selenonucleosides and that conformational bias induced by bulky selenium acted as a decisive factor in the DAST fluorination. Among compounds tested, 2'-F-4'-seleno-ara-C (4a) exhibited highly potent anticancer activity in all cancer cell lines tested and was more potent than ara-C (1).

  DOI：

  10.1021/jm900852b
• 作为产物：
  描述：

  (-)-1-(4-seleno-D-arabinofuranosyl)uracil 、 乙酸酐 在 吡啶 作用下， 生成
  参考文献：
  名称：

  Discovery of a New Template for Anticancer Agents: 2′-deoxy-2′-fluoro-4′-selenoarabinofuranosyl-cytosine (2′-F-4′-Seleno-ara-C)

  摘要：

  The first synthesis of 2'-deoxy-2'-fluoro-4'-selenoarabinofuranosyl pyrimidines as potent anticancer agents was accomplished using the DAST fluorination as a key step. It was first revealed that selenium atom participated in the DAST fluorination of 4'-selenonucleosides and that conformational bias induced by bulky selenium acted as a decisive factor in the DAST fluorination. Among compounds tested, 2'-F-4'-seleno-ara-C (4a) exhibited highly potent anticancer activity in all cancer cell lines tested and was more potent than ara-C (1).

  DOI：

  10.1021/jm900852b