1-((2R,3S,4S,5R)-4-((tetrahydro-2H-pyran-2-yl)oxy)-3-((triethylsilyl)oxy)-5-((trityloxy)methyl)tetrahydroselenophen-2-yl)pyrimidine-2,4(1H,3H)-dione | 1187425-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-((2R,3S,4S,5R)-4-((tetrahydro-2H-pyran-2-yl)oxy)-3-((triethylsilyl)oxy)-5-((trityloxy)methyl)tetrahydroselenophen-2-yl)pyrimidine-2,4(1H,3H)-dione
• CAS: 1187425-04-2
• 化学式: C₃₉H₄₈N₂O₆SeSi
• 分子量: 747.865
• InChiKey: ADILIFNOEYLWQU-XUMBMUMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.85
• 重原子数：
  49.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  91.78
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  三乙基氯硅烷 、 1-(3-O-tetrahydropyranyl-5-O-trityl-4-seleno-D-arabinofuranosyl)uracil 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到1-((2R,3S,4S,5R)-4-((tetrahydro-2H-pyran-2-yl)oxy)-3-((triethylsilyl)oxy)-5-((trityloxy)methyl)tetrahydroselenophen-2-yl)pyrimidine-2,4(1H,3H)-dione
  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