1-(2-chloropyridin-3-ylsulfonyl)-5-fluoropyrimidine-2,4(1H,3H)-dione | 1226645-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(2-chloropyridin-3-ylsulfonyl)-5-fluoropyrimidine-2,4(1H,3H)-dione
• 英文别名: 1-(2-Chloropyridin-3-yl)sulfonyl-5-fluoropyrimidine-2,4-dione
• CAS: 1226645-83-5
• 化学式: C₉H₅ClFN₃O₄S
• 分子量: 305.674
• InChiKey: LILFYCWSQDMABH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 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：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-氟脲嘧啶 、 2-氯吡啶-3-磺酰氯 在 四丁基溴化铵 、 sodium carbonate 作用下， 以 水 、 乙酸乙酯 、 丙酮 为溶剂， 以62%的产率得到1-(2-chloropyridin-3-ylsulfonyl)-5-fluoropyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and Structure–Antitumor Activity Relationship of Sulfonyl 5-Fluorouracil Derivatives

  摘要：

  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.

  DOI：

  10.1080/10426500902754260

文献信息

• 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.