5-(2,4-dichlorophenyl)-1H-indeno[2',1':5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione | 1275613-41-6

• 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-(2,4-dichlorophenyl)-1H-indeno[2',1':5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione
• 英文别名: 2-(2,4-Dichlorophenyl)-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: 1275613-41-6
• 化学式: C₂₀H₉Cl₂N₃O₃
• 分子量: 410.216
• InChiKey: YTPQOCACSVYKIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  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

文献信息

• Tetrazol-Cu(<scp>i</scp>) immobilized on nickel ferrite catalyzed green synthesis of indenopyridopyrimidine derivatives in aqueous media
  作者：Zahra Ghanbari、Hossein Naeimi

  DOI：10.1039/d1ra05889d

  日期：——

  After the initial study of different protocols in the synthesis of indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidines, herein, a new method is presented using cheaper and more accessible starting materials to produce high-efficiency products. In this protocol, the novel nanocatalyst is very effective in the progression of the reaction and increasing the efficiency. This green approach in aqueous media has several

  在对合成茚并[2',1':5,6]吡啶并[2,3- d ]嘧啶的不同方案进行初步研究之后，本文提出了一种使用更便宜、更容易获得的起始材料来生产高- 高效产品。在该协议中，新型纳米催化剂在反应进程和提高效率方面非常有效。与其他方法相比，这种在水介质中的绿色方法具有几个优点，例如更容易后处理、非常温和的反应条件、催化剂的可重复使用性和生态友好性。使用 IR、 1 H NMR、13 C NMR 光谱和 CHN 分析对这种四组分缩合产物进行了评价，并通过 FT-IR、XRD、SEM、EDX、TGA 和 VSM 技术确认了催化剂的结构。
• 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.