5-amino-1-phenylpyrimidine-2,4(1H,3H)-dione | 352017-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-amino-1-phenylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 5-Amino-1-phenyluracil；5-amino-1-phenylpyrimidine-2,4-dione
• CAS: 352017-39-1
• 化学式: C₁₀H₉N₃O₂
• 分子量: 203.2
• InChiKey: MVYMEXXYQHMKLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯酐 、 5-amino-1-phenylpyrimidine-2,4(1H,3H)-dione 以 溶剂黄146 为溶剂， 反应 1.5h， 以60%的产率得到1-phenyl-5-phthalimidopyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Aza analogues of thalidomide

  摘要：

  A synthetic entry to derivatives of the new classes of 5-phthalimidouracils and 5-phthalimidobarbituric acids is reported. These 5-phthalimidopyrimidines as well as phthalimido-2.4-difluorobenzenes were designed as analogues of thalidomide. a we ii known inhibitor of TNF-alpha production. A preliminary in vitro investigation of the compounds as inhibitors of, the TNF-alpha production was performed. Among the compounds of the present series, 5-ethyl-1-phenyl-5-(tetrafluorophthalimido)barbituric acid and 2-(2.4-difluorophenyl)-4,5,6,7-tetrafluoro-1H-isoindole-1,3(2H)-dione were proved to be potent inhibitors. Both compounds showed inhibitory activity in the lower micromolar range on the LPS-induced TNF-alpha production in human monocytes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00323-0
• 作为产物：
  描述：

  1-苯基尿嘧啶 在 氨 、 溴 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 20.0h， 生成 5-amino-1-phenylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Aza analogues of thalidomide

  摘要：

  A synthetic entry to derivatives of the new classes of 5-phthalimidouracils and 5-phthalimidobarbituric acids is reported. These 5-phthalimidopyrimidines as well as phthalimido-2.4-difluorobenzenes were designed as analogues of thalidomide. a we ii known inhibitor of TNF-alpha production. A preliminary in vitro investigation of the compounds as inhibitors of, the TNF-alpha production was performed. Among the compounds of the present series, 5-ethyl-1-phenyl-5-(tetrafluorophthalimido)barbituric acid and 2-(2.4-difluorophenyl)-4,5,6,7-tetrafluoro-1H-isoindole-1,3(2H)-dione were proved to be potent inhibitors. Both compounds showed inhibitory activity in the lower micromolar range on the LPS-induced TNF-alpha production in human monocytes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00323-0