5-(2,4-dichlorophenyl)-5,11-dihydro-1H-indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione | 951922-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 5-(2,4-dichlorophenyl)-5,11-dihydro-1H-indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione
• 英文别名: 5-(2,4-dichlorophenyl)-5,11-dihydro-1H-indeno[2',1':5,6]pyrido[2,3-d]-pyrimidine-2,4,6(3H)-trione；5-(2,4-dichlorophenyl)-5,11-dihydro-1H-indeno[2',1':5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione；2-(2,4-dichlorophenyl)-5,7,9-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),3(8),11,13,15-pentaene-4,6,17-trione
• CAS: 951922-85-3
• 化学式: C₂₀H₁₁Cl₂N₃O₃
• 分子量: 412.232
• InChiKey: ZPZNUNFFIQLICK-UHFFFAOYSA-N

物化性质

• 熔点：
  320-322 °C
• 密度：
  1.67±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  87.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2,4-dichlorophenyl)-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-(2,4-dichlorophenyl)-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
• 作为产物：
  描述：

  4-氨基-2,6-二羟基嘧啶 、 1,3-茚满二酮 、 2,4-二氯苯甲醛 在 氯化胆碱 、 尿素 作用下， 反应 0.5h， 以92%的产率得到5-(2,4-dichlorophenyl)-5,11-dihydro-1H-indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione
  参考文献：
  名称：

  使用由氯化胆碱/尿素组成的深共熔溶剂系统高效合成一系列新型茚并稠合吡啶并[2,3-d]嘧啶

  摘要：

  一系列 13 芳基茚并 [2',1':5,6]pyrido[2,3-d]pyrimidine-2,4,6-(3H,5H,11H)-triones，其中八个是新的，是在由氯化胆碱/尿素组成的低共熔溶剂存在下，通过 1,3-茚二酮、芳醛和 6-氨基嘧啶-2,4(1H,3H)-二酮的三组分反应以高产率区域选择性地合成（ 1:2) 作为催化剂。反应条件温和，不需要额外的催化剂。鉴于深共熔溶剂廉价、无毒和可回收的性质，这些反应条件易于进行且对环境友好。

  DOI：

  10.3184/175815517x14981249895596

文献信息

• 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.
• Efficient synthesis of a novel series of indeno-fused pyrido[2,3-<i>d</i>]pyrimidines using a deep eutectic solvent system comprised of choline chloride/urea
  作者：Mohammad Hakimi Roknabadi、Mohammad Hossein Mosslemin、Razieh Mohebat

  DOI：10.3184/175815517x14981249895596

  日期：2017.7

  A series of 13 aryl indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine-2,4,6-(3H,5H,11H)-triones, eight of which are new, were synthesised regioselectively in high yields by a three-component reaction of 1,3-indanedione, an araldehyde and 6-aminopyrimidin-2,4(1H,3H)-dione in the presence of a deep eutectic solvent comprised of choline chloride/urea (1:2) as the catalyst. The reaction conditions were mild and

  一系列 13 芳基茚并 [2',1':5,6]pyrido[2,3-d]pyrimidine-2,4,6-(3H,5H,11H)-triones，其中八个是新的，是在由氯化胆碱/尿素组成的低共熔溶剂存在下，通过 1,3-茚二酮、芳醛和 6-氨基嘧啶-2,4(1H,3H)-二酮的三组分反应以高产率区域选择性地合成（ 1:2) 作为催化剂。反应条件温和，不需要额外的催化剂。鉴于深共熔溶剂廉价、无毒和可回收的性质，这些反应条件易于进行且对环境友好。