((2R,3S,5R)-3-acetoxy-5-(5-fluoro-3-((methylthio)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate | 1360445-69-7

• 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: ((2R,3S,5R)-3-acetoxy-5-(5-fluoro-3-((methylthio)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate
• CAS: 1360445-69-7
• 化学式: C₁₅H₁₉FN₂O₇S
• 分子量: 390.389
• InChiKey: XZFFXGONUSNLOT-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.25
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  105.83
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  ((2R,3S,5R)-3-acetoxy-5-(5-fluoro-3-((methylthio)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate 在 N-氯代丁二酰亚胺 、 三甲基氯硅烷 、 sodium azide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 ((2R,3S,5R)-3-acetoxy-5-(3-(azidomethyl)-5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate
  参考文献：
  名称：

  Reductive activation of 5-fluorodeoxyuridine prodrug possessing azide methyl group by hypoxic X-irradiation

  摘要：

  We prepared a 5-fluorodeoxyuridine (5-FdUrd) derivative possessing azide methyl group (N-3-FdUrd) as a novel radiation-activated prodrug. The parent antitumor agent, 5-FdUrd, was released efficiently from N-3-FdUrd by hypoxic X-irradiation. On the other hand, the activation of N-3-FdUrd was suppressed upon X-irradiation under aerobic conditions. A biological assay using A549 cells revealed that the cytotoxicity of N-3-FdUrd was significantly enhanced by hypoxic X-irradiation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.106
• 作为产物：
  描述：

  氯甲基甲硫醚 、 3,5-二-o-乙酰基-5-氟-2-脱氧尿苷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以78%的产率得到((2R,3S,5R)-3-acetoxy-5-(5-fluoro-3-((methylthio)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate
  参考文献：
  名称：

  Reductive activation of 5-fluorodeoxyuridine prodrug possessing azide methyl group by hypoxic X-irradiation

  摘要：

  We prepared a 5-fluorodeoxyuridine (5-FdUrd) derivative possessing azide methyl group (N-3-FdUrd) as a novel radiation-activated prodrug. The parent antitumor agent, 5-FdUrd, was released efficiently from N-3-FdUrd by hypoxic X-irradiation. On the other hand, the activation of N-3-FdUrd was suppressed upon X-irradiation under aerobic conditions. A biological assay using A549 cells revealed that the cytotoxicity of N-3-FdUrd was significantly enhanced by hypoxic X-irradiation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.106