1-(4-bromophenylsulfonyl)-5-fluoropyrimidine-2,4(1H,3H)-dione | 56059-13-3

• 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: 1-(4-bromophenylsulfonyl)-5-fluoropyrimidine-2,4(1H,3H)-dione
• 英文别名: 1-(4-bromo-benzenesulfonyl)-5-fluoro-1H-pyrimidine-2,4-dione；1-(p-bromobenzenesulfonyl)-5-fluorouracil；1-(p-Brombenzolsulfonyl)-5-fluoruracil；1-(4-Bromophenyl)sulfonyl-5-fluoropyrimidine-2,4-dione
• CAS: 56059-13-3
• 化学式: C₁₀H₆BrFN₂O₄S
• 分子量: 349.137
• InChiKey: ODPXOUFMBOFZCU-UHFFFAOYSA-N

物化性质

• 熔点：
  201-203 °C
• 密度：
  1.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  91.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenylsulfonyl)-5-fluoropyrimidine-2,4(1H,3H)-dione 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 四丁基溴化铵 sodium hydroxide 作用下， 以 氯仿 、 水 为溶剂， 反应 2.5h， 以50.8%的产率得到[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-(4-bromophenyl)sulfonyl-5-fluoro-2,6-dioxopyrimidin-1-yl]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  1-芳基磺酰基-3-N-(β-D-ACETYLGLYCOPYRANOS-1-YL)-5-氟尿嘧啶和抗肿瘤活性的合成

  摘要：

  通过1-芳基磺酰基-5-氟尿嘧啶与溴乙酰葡萄糖或溴乙酰木糖在相转移催化下反应合成1-芳磺酰基-5-氟尿嘧啶的15种糖苷。它们的结构经IR、1HNMR和元素分析证实。体外试验的初步结果表明，其中一些具有一定的抗肿瘤活性。

  DOI：

  10.1081/scc-100000181
• 作为产物：
  描述：

  5-氟脲嘧啶 、 4-溴苯磺酰氯 在 四丁基溴化铵 、 sodium carbonate 作用下， 以 水 、 乙酸乙酯 、 丙酮 为溶剂， 以52%的产率得到1-(4-bromophenylsulfonyl)-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

• US3971784A
  申请人：——

  公开号：US3971784A

  公开（公告）日：1976-07-27
• SYNTHESIS OF 1-ARYLSULFONYL-3-N-(β-D-ACETYLGLYCOPYRANOS-1-YL)-5-FLUOROURACIL AND ANTITUMOR ACTIVITIES
  作者：Chang-Jun Sun、Ji-Ming Zhang、Shuang-Jia Wang、Fen-Yan Zhou、Yu-Xin Qi、Min Lu

  DOI：10.1081/scc-100000181

  日期：2001.1

  Fifteen glycosides of 1-arylsulfonyl-5-fluorouracil were synthesized by the reaction of 1-arylsulfonyl-5-fluorouracil with bromoacetylglucose or bromoacetylxylose under phase transfer catalysis. Their structures were confirmed by IR, 1HNMR, and elementary analysis. Preliminary results of in vitro tests showed that some of them have certain antitumor activities.

  通过1-芳基磺酰基-5-氟尿嘧啶与溴乙酰葡萄糖或溴乙酰木糖在相转移催化下反应合成1-芳磺酰基-5-氟尿嘧啶的15种糖苷。它们的结构经IR、1HNMR和元素分析证实。体外试验的初步结果表明，其中一些具有一定的抗肿瘤活性。
• 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.