3-(azidomethyl)-5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione | 1360445-71-1

• 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: 3-(azidomethyl)-5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 1360445-71-1
• 化学式: C₁₀H₁₂FN₅O₅
• 分子量: 301.234
• InChiKey: ADKTWKZXECATAF-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3,5-二-o-乙酰基-5-氟-2-脱氧尿苷 在 甲醇 、 N-氯代丁二酰亚胺 、 三甲基氯硅烷 、 sodium azide 、 水 、 sodium hydride 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 55.0h， 生成 3-(azidomethyl)-5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
  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

文献信息

• Reductive activation of 5-fluorodeoxyuridine prodrug possessing azide methyl group by hypoxic X-irradiation
  作者：Kazuhito Tanabe、Jin Ishizaki、Yuichirou Ando、Takeo Ito、Sei-ichi Nishimoto

  DOI：10.1016/j.bmcl.2011.12.106

  日期：2012.2

  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.