5-bromo-1-phenyl pyrimidine-2, 4 (1H, 3H)-dione | 53369-66-7

• 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-bromo-1-phenyl pyrimidine-2, 4 (1H, 3H)-dione
• 英文别名: 5-Bromo-1-phenylpyrimidine-2,4-dione
• CAS: 53369-66-7
• 化学式: C₁₀H₇BrN₂O₂
• 分子量: 267.082
• InChiKey: IWOSQFLEGHWABZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-1-phenyl pyrimidine-2, 4 (1H, 3H)-dione 在 氨 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以38%的产率得到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
• 作为产物：
  描述：

  苯基脲 在 溴 、 sodium hydride 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 反应 1.75h， 生成 5-bromo-1-phenyl pyrimidine-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

• Synthesis and evaluation as PDE4 inhibitors of pyrimidine-2,4-dione derivatives
  作者：Maria P. Giovannoni、Alessia Graziano、Rosanna Matucci、Marta Nesi、Nicoletta Cesari、Claudia Vergelli、Claudio Biancalani、Letizia Crocetti、Agostino Cilibrizzi、Vittorio Dal Piaz

  DOI：10.1002/ddr.20395

  日期：2011.5

  nitraquazone analogs with a pyrimidindione core was synthesized and tested for inhibitory activity on PDE4, selectivity versus PDE3 and PDE5 and for affinity towards the rolipram high‐affinity binding site (HARBS). The 5‐anilino derivatives 13–18 showed the best profile combining appreciable PDE4 inhibitory activity (IC50 = 5–14 µM) with a good selectivity toward PDE3 and PDE5. The same compounds demonstrate

  合成了一系列具有嘧啶二酮核心的硝唑酮类似物，并测试了其对PDE4的抑制活性，对PDE3和PDE5的选择性以及对咯利普兰高亲和力结合位点（HARBS）的亲和力。5-苯胺基衍生物13–18表现出最好的特性，结合了可观的PDE4抑制活性（IC 50 = 5–14 µM）和对PDE3和PDE5的良好选择性。相同的化合物显示出对HARBS位点的低亲和力，IC 50值为12–69 µM（对于Rolipram的IC 50 = 3.6 nM）。Drug Dev Res 72：274–288，2011。©2010 Wiley-Liss，Inc.
• Sagheer, Tahira; Ehsan, Shahana; Akbar, Wajiha, Journal of the Chemical Society of Pakistan, 2018, vol. 40, # 4, p. 742 - 748
  作者：Sagheer, Tahira、Ehsan, Shahana、Akbar, Wajiha、Faisal, Saniya

  DOI：——

  日期：——
• Moltke-Leth, Claus; Joergensen, Karl Anker, Journal of the Chemical Society. Perkin transactions II, 1993, # 8, p. 1487 - 1490
  作者：Moltke-Leth, Claus、Joergensen, Karl Anker

  DOI：——

  日期：——
• Moltke-Leth, Claus; Joergensen, Karl Anker, Acta Chemica Scandinavica, 1993, vol. 47, # 11, p. 1117 - 1121
  作者：Moltke-Leth, Claus、Joergensen, Karl Anker

  DOI：——

  日期：——
• 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.

表征谱图