5-(4-methoxyphenyl)-5,11-dihydro-1H-indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione | 24680-26-0

• 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-(4-methoxyphenyl)-5,11-dihydro-1H-indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione
• 英文别名: 5-(4-methoxyphenyl)-5,11-dihydro-1H-indeno[2',1':5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione；5-(4-methoxyphenyl)-1H-indeno[2',1':5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione；5-(4-methoxy-phenyl)-5,11-dihydro-1H-indeno[2',1':5,6]pyrido[2,3-d]pyrimidine-2,4,6-trione；2,4-dihydroxy-5-(4-methoxyphenyl)-5,11-dihydro-6H-indeno[2',1':5,6]pyrido[2,3-d]pyrimidin-6-one；2-(4-methoxyphenyl)-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: 24680-26-0
• 化学式: C₂₁H₁₅N₃O₄
• 分子量: 373.368
• InChiKey: VTMPHROQCDZGEN-UHFFFAOYSA-N

物化性质

• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  96.5
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-氨基-2,6-二羟基嘧啶 、 1,3-茚满二酮 、 4-甲氧基苯甲醛 在 氧气 作用下， 以 乙二醇 、 溶剂黄146 为溶剂， 反应 4.0h， 以72%的产率得到5-(4-methoxyphenyl)-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：

  Three-component synthesis and anticancer evaluation of polycyclic indenopyridines lead to the discovery of a novel indenoheterocycle with potent apoptosis inducing properties

  摘要：

  研究人员对茚-1,3-二酮、一种醛和一种含胺芳香化合物的多组分反应进行了研究，该反应可生成以茚并吡啶为基础的杂环药物支架。研究发现，如果在反应混合物中通入氧气，可促进中间的含二氢吡啶化合物氧化成芳香族对应化合物，从而显著提高产量。对反应范围的研究表明，甲醛以及各种脂肪族、芳香族和杂芳香族醛类都能很好地用作醛组分。此外，取代的苯胺和各种氨基杂环也可作为含胺组分用于该过程。通过对合成的化合物库进行初步生物评估，发现了一种嘧啶基多环化合物，它对人类 T 细胞白血病细胞系的毒性和诱导细胞凋亡的特性可与抗癌药物依托泊苷相媲美。

  DOI：

  10.1039/b713820b

文献信息

• 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。