1-((2R,4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-(2-(3,4-dimethoxyphenyl)-1,3-dithian-2-yl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-((2R,4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-(2-(3,4-dimethoxyphenyl)-1,3-dithian-2-yl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 1-[(2R,4S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[2-(3,4-dimethoxyphenyl)-1,3-dithian-2-yl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₂₈H₄₂N₂O₆S₂Si
• 分子量: 594.869
• InChiKey: XOVCHKAKMMRPCH-TUACAJSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-((2R,4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-(2-(3,4-dimethoxyphenyl)-1,3-dithian-2-yl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以97%的产率得到1-((2R,4S,5S)-4-(2-(3,4-dimethoxyphenyl)-1,3-dithian-2-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Design, synthesis, and evaluation of DNA topoisomerase II-targeted nucleosides

  摘要：

  We developed novel nucleoside-based topoisomerase II selective inhibitors and showed that small structural units, such as catechols, are essential for DNA topoisomerase II inhibitory activity. Moreover, nucleoside analogues containing TBS and 1,3-dithian moieties had potent and selective DNA topoisomerase II inhibitory activities. In further experiments, compound 25b having a beta configuration of the thymine moiety showed relatively strong growth inhibitory activity against cancer cell lines, and was more potent against all cancer cell lines than compound 26b, which carries a thymine moiety in the alpha configuration. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.06.001
• 作为产物：
  描述：

  2-(3,4-二甲氧基-苯基)-[1,3]二噻烷 在 吡啶 、 正丁基锂 、 N,O-双三甲硅基乙酰胺 、 二异丁基氢化铝 、 bovine serum albumin 作用下， 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 生成 1-((2R,4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-(2-(3,4-dimethoxyphenyl)-1,3-dithian-2-yl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 、 1-((2S,4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-(2-(3,4-dimethoxyphenyl)-1,3-dithian-2-yl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Design, synthesis, and evaluation of DNA topoisomerase II-targeted nucleosides

  摘要：

  We developed novel nucleoside-based topoisomerase II selective inhibitors and showed that small structural units, such as catechols, are essential for DNA topoisomerase II inhibitory activity. Moreover, nucleoside analogues containing TBS and 1,3-dithian moieties had potent and selective DNA topoisomerase II inhibitory activities. In further experiments, compound 25b having a beta configuration of the thymine moiety showed relatively strong growth inhibitory activity against cancer cell lines, and was more potent against all cancer cell lines than compound 26b, which carries a thymine moiety in the alpha configuration. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.06.001