5-fluoro-1-(3-nitrophenylsulfonyl)pyrimidine-2,4(1H,3H)-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-fluoro-1-(3-nitrophenylsulfonyl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 5-fluoro-1-(3-nitrophenylsulfonyl)uracil；5-Fluoro-1-(3-nitrophenyl)sulfonylpyrimidine-2,4-dione
• 化学式: C₁₀H₆FN₃O₆S
• 分子量: 315.239
• InChiKey: NRLFEACIWPGSDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-氟脲嘧啶 、 3-硝基苯磺酰氯 在 三乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以37%的产率得到5-fluoro-1-(3-nitrophenylsulfonyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  具有含硫取代基的5-氟尿嘧啶和5-氟尿嘧啶衍生物的γ辐射分解

  摘要：

  在水合条件下，研究了8个在1位具有磺酰基取代基的5-氟尿嘧啶（5-FU）衍生物和5个具有硫脲基取代基的5-氟尿嘧啶（5-FUR）衍生物的γ分解反应。电子（E水溶液- ）和羟基自由基（HO·）成为主要的反应性物质。对5-FU和5-FUR衍生物进行放射水解，分别得到5-FU和5-FUR。反应的效率取决于反应性物质的性质以及取代基的性质。讨论了γ-辐射分解反应的反应性特征。

  DOI：

  10.1002/jhet.5570310213

文献信息

• γ-Radiolysis of 5-fluorouracil and 5-fluorouridine derivatives having sulfur-containing substituents
  作者：Tokuyuki Kuroda、Koji Hisamura、Hiroshi Nishikawa、Nobuhiro Nakamizo、Yoshio Otsuji

  DOI：10.1002/jhet.5570310213

  日期：1994.3

  γ-Radiolysis reactions of eight 5-fluorouracil (5-FU) derivatives having sulfonyl group-containing substituents at the 1-position and five 5-fluorouridine (5-FUR) derivatives having thioureido group-containing substituents were studied under the conditions where hydrated electron (eaq−) and hydroxyl radical (HO·) become the principal reactive species. The 5-FU and 5-FUR derivatives were radiolyzed

  在水合条件下，研究了8个在1位具有磺酰基取代基的5-氟尿嘧啶（5-FU）衍生物和5个具有硫脲基取代基的5-氟尿嘧啶（5-FUR）衍生物的γ分解反应。电子（E水溶液- ）和羟基自由基（HO·）成为主要的反应性物质。对5-FU和5-FUR衍生物进行放射水解，分别得到5-FU和5-FUR。反应的效率取决于反应性物质的性质以及取代基的性质。讨论了γ-辐射分解反应的反应性特征。
• Synthesis and Structure–Antitumor Activity Relationship of Sulfonyl 5-Fluorouracil Derivatives
  作者：Xiaowei Yan、Yong Hou、Fan Chen、Kejian Zhao、Maolin Hu

  DOI：10.1080/10426500902754260

  日期：2009.12.29

  Novel sulfonyl 5-fluorouracil derivatives 2 (5-fluoro-1-(arylsulfonyl) pyrimidine-2,4(1H,3H)-diones) have been synthesized via the reaction of 5-fluorouracil with sulfonyl chloride. Their chemical structures were confirmed by means of (HNMR)-H-1, C-13 NMR, IR, mass spectra, and elemental analyses, and, in the case of 2a, its structure was established by single crystal X-ray diffraction. Some of the compounds were assayed for anticancer (HL-60 and BEL-7402 cells) activities. Structure-activity relationship (SAR) analysis discovered that the anticancer activity was related to the configuration, and that electron-withdrawing groups at 2-position or 4-position on the aryl group of arylsulfonyl derivatives of 5-fluorouracil could enhance the anticancer activity against the BEL-7402 cells.