5-(4-fluorophenyl)-1H-indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione | 933234-21-0

• 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: 5-(4-fluorophenyl)-1H-indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione
• 英文别名: 5-(4-fluorophenyl)-1H-indeno[2',1':5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione；2-(4-fluorophenyl)-5,7,9-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),2,8,11,13,15-hexaene-4,6,17-trione
• CAS: 933234-21-0
• 化学式: C₂₀H₁₀FN₃O₃
• 分子量: 359.316
• InChiKey: XLKUPGYCPQCIML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-(4-fluorophenyl)-5,11-dihydro-1H-indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione 在 四氯苯醌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.07h， 以95%的产率得到5-(4-fluorophenyl)-1H-indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione
  参考文献：
  名称：

  Structural Simplification of Bioactive Natural Products with Multicomponent Synthesis. 3. Fused Uracil-Containing Heterocycles as Novel Topoisomerase-Targeting Agents

  摘要：

  After the initial discovery of antiproliferative and apoptosis-inducing properties of a camptothecin-inspired pentacycle based on a 1H-indeno[2',1':5,6]dihydropyrido[2,3-d]pyrimidine scaffold, a library of its analogues as well as their oxidized planar counterparts were prepared utilizing a practical multicomponent synthetic protocol. The synthesized compounds exhibited submicromolar to low micromolar antiproliferative potencies toward a panel of human cancer cell lines. Biochemical experiments are consistent with the dihydropyridine library members undergoing intracellular oxidation to the corresponding planar pyridines, which then inhibit topoisomerase II activity, leading to inhibition of proliferation and cell death. Because of facile synthetic preparation and promising antitopoisomerase activity, both the dihydropyridine and planar pyridine-based compounds represent a convenient starting point for anticancer drug discovery.

  DOI：

  10.1021/jm1009428

文献信息

• Graphene Oxide: A Carbocatalyst for the One-Pot Multicomponent Synthesis of 5-Aryl-1H-Indeno[2’,1’:5,6]Pyrido[2,3-d]Pyrimidine-2,4,6(3H)-Trione
  作者：Hamid Reza Dehghanpour、Mohammad H. Mosslemin、Razieh Mohebat

  DOI：10.3184/174751918x15161933697835

  日期：2018.1

  and efficient method is described for the synthesis of 5-aryl-1H-indeno[2’,1’:5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione via one-pot multicomponent reaction of indane-1,3-dione, arylaldehydes and 6-aminopyrimidin-2,4(1H,3H)-dione in presence of catalytic amount of graphene oxide in water. Graphene oxide is a versatile carbocatalyst and this is the first report on its application in a pyrido[2,3-d]pyrimidine

  描述了一种简单、直接且有效的方法来合成 5-芳基-1H-茚[2',1':5,6]吡啶并[2,3-d]嘧啶-2,4,6(3H)-在水中催化量的氧化石墨烯存在下，茚满-1,3-二酮、芳醛和 6-氨基嘧啶-2,4(1H,3H)-二酮的一锅多组分反应生成三酮。氧化石墨烯是一种多功能的碳催化剂，这是首次报道其在吡啶并[2,3-d]嘧啶合成中的应用。良好的产量、​​使用现成的起始材料、操作简单、易于处理和环保可重复使用的催化剂是该协议的主要特点。
• Structural Simplification of Bioactive Natural Products with Multicomponent Synthesis. 3. Fused Uracil-Containing Heterocycles as Novel Topoisomerase-Targeting Agents
  作者：Nikolai M. Evdokimov、Severine Van slambrouck、Petra Heffeter、Lee Tu、Benjamin Le Calvé、Delphine Lamoral-Theys、Carla J. Hooten、Pavel Y. Uglinskii、Snezna Rogelj、Robert Kiss、Wim F. A. Steelant、Walter Berger、Jeremy J. Yang、Cristian G. Bologa、Alexander Kornienko、Igor V. Magedov

  DOI：10.1021/jm1009428

  日期：2011.4.14

  After the initial discovery of antiproliferative and apoptosis-inducing properties of a camptothecin-inspired pentacycle based on a 1H-indeno[2',1':5,6]dihydropyrido[2,3-d]pyrimidine scaffold, a library of its analogues as well as their oxidized planar counterparts were prepared utilizing a practical multicomponent synthetic protocol. The synthesized compounds exhibited submicromolar to low micromolar antiproliferative potencies toward a panel of human cancer cell lines. Biochemical experiments are consistent with the dihydropyridine library members undergoing intracellular oxidation to the corresponding planar pyridines, which then inhibit topoisomerase II activity, leading to inhibition of proliferation and cell death. Because of facile synthetic preparation and promising antitopoisomerase activity, both the dihydropyridine and planar pyridine-based compounds represent a convenient starting point for anticancer drug discovery.