1,3-bis[5-fluoro-1-(β-2'-deoxy-3',5'-di-O-acetylribofuranosyl)-2,4-dioxopyrimidinyl]-propane | 1395918-66-7

• 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: 1,3-bis[5-fluoro-1-(β-2'-deoxy-3',5'-di-O-acetylribofuranosyl)-2,4-dioxopyrimidinyl]-propane
• CAS: 1395918-66-7
• 化学式: C₂₉H₃₄F₂N₄O₁₄
• 分子量: 700.604
• InChiKey: GTLAVNXLHAGSIM-NCIBGLJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.73
• 重原子数：
  49.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  211.66
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  1,3-bis[5-fluoro-1-(β-2'-deoxy-3',5'-di-O-acetylribofuranosyl)-2,4-dioxopyrimidinyl]-propane 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 以100%的产率得到1,3-bis[5-fluoro-1-(β-2'-deoxyribofuranosyl)-2,4-dioxopyrimidinyl]propane
  参考文献：
  名称：

  Synthesis and one-electron reduction characteristics of radiation-activated prodrugs possessing two 5-fluorodeoxyuridine units

  摘要：

  Two molecules of an antitumor agent, 5-fluorodeoxyuridine (5-FdUrd), were connected by a 2-oxoalkyl linker (Oxo-linker) at the N(3) position to obtain radiation-activated prodrugs, FdUrd(2) A and FdUrd(2) B. The prodrugs in this study released 5-FdUrd via one-electron reduction initiated by hypoxic X-irradiation. The release of 5-FdUrd from FdUrd(2) A and FdUrd(2) B proceeded more efficiently than that of previous prodrug, Oxo-FdUrd, which possessed one molecule of 5-FdUrd. FdUrd(2) A exhibited increased cytotoxicity against A549 cells when the FdUrd(2) A solution had been irradiated with a large dose of X-rays before administration to the cells. However, we observed no effect on cytotoxicity when the cells were X-irradiated under hypoxic conditions in the presence of FdUrd(2) A because the amount of 5-FdUrd released in the cells seemed to be too low to induce cytotoxic activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.008
• 作为产物：
  描述：

  1,3-二溴丙烷 、 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 24.25h， 以63%的产率得到1,3-bis[5-fluoro-1-(β-2'-deoxy-3',5'-di-O-acetylribofuranosyl)-2,4-dioxopyrimidinyl]-propane
  参考文献：
  名称：

  Synthesis and one-electron reduction characteristics of radiation-activated prodrugs possessing two 5-fluorodeoxyuridine units

  摘要：

  Two molecules of an antitumor agent, 5-fluorodeoxyuridine (5-FdUrd), were connected by a 2-oxoalkyl linker (Oxo-linker) at the N(3) position to obtain radiation-activated prodrugs, FdUrd(2) A and FdUrd(2) B. The prodrugs in this study released 5-FdUrd via one-electron reduction initiated by hypoxic X-irradiation. The release of 5-FdUrd from FdUrd(2) A and FdUrd(2) B proceeded more efficiently than that of previous prodrug, Oxo-FdUrd, which possessed one molecule of 5-FdUrd. FdUrd(2) A exhibited increased cytotoxicity against A549 cells when the FdUrd(2) A solution had been irradiated with a large dose of X-rays before administration to the cells. However, we observed no effect on cytotoxicity when the cells were X-irradiated under hypoxic conditions in the presence of FdUrd(2) A because the amount of 5-FdUrd released in the cells seemed to be too low to induce cytotoxic activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.008