5-(3-nitrophthalimido)-1-phenylpyrimidine-2,4(1H,3H)-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 5-(3-nitrophthalimido)-1-phenylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 2-(2,4-Dioxo-1-phenylpyrimidin-5-yl)-4-nitroisoindole-1,3-dione
• 化学式: C₁₈H₁₀N₄O₆
• 分子量: 378.301
• InChiKey: SLKQHGRUGHPJFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯基脲 在 氨 、 溴 、 sodium hydride 作用下， 以 1,4-二氧六环 、 甲醇 、 溶剂黄146 为溶剂， 反应 38.75h， 生成 5-(3-nitrophthalimido)-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

文献信息

• Aza analogues of thalidomide
  作者：Michael Gütschow、Thomas Hecker、Andrea Thiele、Sunna Hauschildt、Kurt Eger

  DOI：10.1016/s0968-0896(00)00323-0

  日期：2001.4

  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.