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

• 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-methoxyphenyl)-1H-indeno[2',1':5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione
• 英文别名: 2-(4-methoxyphenyl)-5,7,9-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),2,8,11,13,15-hexaene-4,6,17-trione
• 化学式: C₂₁H₁₃N₃O₄
• 分子量: 371.352
• InChiKey: OKLOUEYIHJIHLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  97.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-(4-methoxyphenyl)-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97%的产率得到5-(4-methoxyphenyl)-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。
• Nano Fe2O3@SiO2–SO3H: efficient catalyst for the multi-component preparation of indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione derivatives
  作者：Majid Ghashang、Sai Guhanathan、S. Sheik Mansoor

  DOI：10.1007/s11164-017-3073-6

  日期：2017.12

  aldehydes, 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione and 1H-indene-1,3(2H)-dione using nano Fe2O3@SiO2–SO3H as a catalyst is described. The products are a variety of indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione derivatives. The effect of the solvent on the product selectivity was investigated. The morphology, particle size distribution, and some properties of Fe2O3@SiO2–SO3H nanopowders

  使用纳米Fe 2进行结构多样的芳基醛，6-氨基-1,3-二甲基嘧啶-2,4（1H，3H）-二酮和1H-茚-1,3（2H）-二酮的高效多组分反应ø 3 @SiO 2 -SO 3 H作为催化剂进行说明。产物是各种茚并[2'，1'：5,6]吡啶[2,3-d]嘧啶-2,4,6（3H）-三酮衍生物。研究了溶剂对产物选择性的影响。通过透射电子显微镜（TEM），动态光散射（DLS），X射线粉末衍射（XRD），Fe 2 O 3 @SiO 2 -SO 3 H纳米粉体的形貌，粒度分布和某些性能。N 2 吸附-解吸等温线和热重分析（TGA）技术。
• 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。