2'-deoxy-5-fluoro-3-(2'-oxocyclobutyl)uridine | 294840-26-9

• 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: 2'-deoxy-5-fluoro-3-(2'-oxocyclobutyl)uridine
• 英文别名: 5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-(2-oxocyclobutyl)pyrimidine-2,4-dione
• CAS: 294840-26-9
• 化学式: C₁₃H₁₅FN₂O₆
• 分子量: 314.27
• InChiKey: SUPQACSTEIBPPA-LTYKLIDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

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 sodium hydroxide 、 水 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.17h， 生成 2'-deoxy-5-fluoro-3-(2'-oxocyclobutyl)uridine
  参考文献：
  名称：

  One-Electron reduction characteristics of N(3)-Substituted 5-fluorodeoxyuridines synthesized as radiation-Activated prodrugs

  摘要：

  We designed and synthesized N(3)-substituted 5-fluorodeoxyuridines as radiation-activated prodrugs of the antitumor agent, 5-fluorodeoxyuridine (5-FdUrd). A series of 5-FdUrd derivatives possessing a 2-oxoalkyl group at the N(3)-position released 5-FdUrd in good yield via one-electron reduction initiated by hypoxic irradiation. Cytotoxicity of the 5-FdUrd derivative possessing the 2-oxocyclopentyl group (3d) was low, but was enhanced by hypoxic irradiation resulting in 5-FdUrd release. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.001

文献信息

• One-Electron reduction characteristics of N(3)-Substituted 5-fluorodeoxyuridines synthesized as radiation-Activated prodrugs
  作者：Kazuhito Tanabe、Youhei Mimasu、Akira Eto、Yukihiro Tachi、Shingo Sakakibara、Mayuko Mori、Hiroshi Hatta、Sei-ichi Nishimoto

  DOI：10.1016/j.bmc.2003.08.001

  日期：2003.10

  We designed and synthesized N(3)-substituted 5-fluorodeoxyuridines as radiation-activated prodrugs of the antitumor agent, 5-fluorodeoxyuridine (5-FdUrd). A series of 5-FdUrd derivatives possessing a 2-oxoalkyl group at the N(3)-position released 5-FdUrd in good yield via one-electron reduction initiated by hypoxic irradiation. Cytotoxicity of the 5-FdUrd derivative possessing the 2-oxocyclopentyl group (3d) was low, but was enhanced by hypoxic irradiation resulting in 5-FdUrd release. (C) 2003 Elsevier Ltd. All rights reserved.