2-amino-5,10-dihydro-5,10-dioxo-4(pyridine-3-yl)-4H-benzo[g]chromene-3-carbonitrile | 331859-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-amino-5,10-dihydro-5,10-dioxo-4(pyridine-3-yl)-4H-benzo[g]chromene-3-carbonitrile
• 英文别名: 2-amino-5,10-dioxo-4-(pyridin-3-yl)-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile；2-amino-5,10-dioxo-4-pyridin-3-yl-4H-benzo[g]chromene-3-carbonitrile
• CAS: 331859-80-4
• 化学式: C₁₉H₁₁N₃O₃
• 分子量: 329.315
• InChiKey: IKSQLSIBENYRML-UHFFFAOYSA-N

物化性质

• 沸点：
  652.0±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 2-amino-5,10-dihydro-5,10-dioxo-4(pyridine-3-yl)-4H-benzo[g]chromene-3-carbonitrile 以 丙酮 为溶剂， 反应 0.5h， 以100%的产率得到(3‑(2‑amino‑3‑cyano‑5,10‑dihydro‑5,10‑dioxo‑4H‑benzo[g]chromen‑4‑yl)pyridine)(dichlorido)(η⁵‑p‑cymene)ruthenium(II)
  参考文献：
  名称：

  新的4-（吡啶基）-4 H-苯并[g]亚甲基-5,10-二酮钌（II）配合物诱导518A2黑色素瘤细胞衰老

  摘要：

  使具有细胞毒性的劳森酮衍生物2-氨基-5,10-二氢-5,10-二氧代-4（吡啶-3-基）-4 H-苯并[ g ]亚甲基-3-甲腈5与[Ru（对-cymene）Cl 2 ] 2提供一种新的Ru（II）“钢琴凳”复合物6，该化合物与它的配体5的区别在于在MTT细胞毒性试验中对高侵袭性518A2黑色素瘤细胞的选择性比人类真皮成纤维细胞高。前者诱导衰老而不是凋亡。DNA可能是复合物6的细胞靶标因为它在体外可能以非共价方式与线性和环状双链DNA结合，并且在处理过的518A2黑色素瘤细胞核的裂解物中发现了钌。它也导致这些细胞中活性氧的增加五倍，这是由于循环伏安法显示的更持久的氧化还原循环而引起的。

  DOI：

  10.1007/s00775-019-01677-y
• 作为产物：
  描述：

  3-吡啶甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 2-amino-5,10-dihydro-5,10-dioxo-4(pyridine-3-yl)-4H-benzo[g]chromene-3-carbonitrile
  参考文献：
  名称：

  Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-Pyrano-[2,3-b]naphthoquinones with anticancer activity

  摘要：

  4H-Pyrano-[2,3-b]naphthoquinone is a structural motif commonly found in natural products manifesting anticancer activities. As part of a program aimed at structural simplification of bioactive natural products utilizing multicomponent synthetic processes, we developed a compound library based on this heterocyclic scaffold. We found that several library members displayed low micromolar antiproliferative activity and induced apoptosis in human cancer cells. Selected compounds showed promising activity against cancer cell lines resistant to proapoptotic stimuli, demonstrating their potential in treating cancers with dismal prognoses. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.073

文献信息

• A novel Hercynite‐supported tetradentate Schiff base complex of manganese catalyzed one‐pot annulation reactions
  作者：Masoud Mohammadi、Arash Ghorbani‐Choghamarani

  DOI：10.1002/aoc.6905

  日期：2022.12

  The present study is the first report on the synthesis and catalytic performance of Hercynite nanoparticles capped with a novel Schiff base–manganese(II) complex brought from a synthetic procedure. The solid support and the catalyst were characterized using various analytical techniques. The characterization results suggest excellent dispersibility, stability, high Mn content under the catalyst surface

  本研究首次报道了海辛纳米粒子的合成和催化性能，该纳米粒子覆盖了从合成过程中获得的新型席夫碱-锰 (II) 络合物。使用各种分析技术表征固体载体和催化剂。表征结果表明具有优异的分散性、稳定性、催化剂表面下的高锰含量和小尺寸的催化剂，从而具有优异的催化活性和选择性。此外，该催化剂被证明是可持续和可回收的，可用于在环境条件下快速合成各种色烯和吡喃环化的杂环。研究并优化了各种关键催化参数的影响。反应范围扩展到各种芳基醛和酮-烯醇互变异构对（2-羟基-1，以优异的产率 (82-99%) 和低反应时间 (10-115 分钟) 获得H-色烯和 2-氨基-3-氰基-4 H-吡喃产物。值得注意的是，该催化剂具有磁性、成本效益和无毒特性，从而具有高回收效率（5 个循环）。
• A new 4-(pyridinyl)-4H-benzo[g]chromene-5,10-dione ruthenium(II) complex inducing senescence in 518A2 melanoma cells
  作者：Madeleine Gold、Yusufi Mujahid、Khursheed Ahmed、Hana Kostrhunova、Jana Kasparkova、Viktor Brabec、Bernhard Biersack、Rainer Schobert

  DOI：10.1007/s00775-019-01677-y

  日期：2019.8

  2-Amino-5,10-dihydro-5,10-dioxo-4(pyridine-3-yl)-4H-benzo[g]chromene-3-carbonitrile 5, a cytotoxic lawsone derivative, was reacted with [Ru(p-cymene)Cl2]2 to afford a new Ru(II) ‘piano-stool’ complex 6 which differed from its ligand 5 by a greater selectivity for highly invasive 518A2 melanoma cells over human dermal fibroblasts in MTT cytotoxicity assays, and by inducing senescence rather than apoptosis

  使具有细胞毒性的劳森酮衍生物2-氨基-5,10-二氢-5,10-二氧代-4（吡啶-3-基）-4 H-苯并[ g ]亚甲基-3-甲腈5与[Ru（对-cymene）Cl 2 ] 2提供一种新的Ru（II）“钢琴凳”复合物6，该化合物与它的配体5的区别在于在MTT细胞毒性试验中对高侵袭性518A2黑色素瘤细胞的选择性比人类真皮成纤维细胞高。前者诱导衰老而不是凋亡。DNA可能是复合物6的细胞靶标因为它在体外可能以非共价方式与线性和环状双链DNA结合，并且在处理过的518A2黑色素瘤细胞核的裂解物中发现了钌。它也导致这些细胞中活性氧的增加五倍，这是由于循环伏安法显示的更持久的氧化还原循环而引起的。
• Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-Pyrano-[2,3-b]naphthoquinones with anticancer activity
  作者：Igor V. Magedov、Artem S. Kireev、Aaron R. Jenkins、Nikolai M. Evdokimov、Dustin T. Lima、Paul Tongwa、Jeff Altig、Wim F. A. Steelant、Severine Van slambrouck、Mikhail Yu. Antipin、Alexander Kornienko

  DOI：10.1016/j.bmcl.2012.06.073

  日期：2012.8

  4H-Pyrano-[2,3-b]naphthoquinone is a structural motif commonly found in natural products manifesting anticancer activities. As part of a program aimed at structural simplification of bioactive natural products utilizing multicomponent synthetic processes, we developed a compound library based on this heterocyclic scaffold. We found that several library members displayed low micromolar antiproliferative activity and induced apoptosis in human cancer cells. Selected compounds showed promising activity against cancer cell lines resistant to proapoptotic stimuli, demonstrating their potential in treating cancers with dismal prognoses. (c) 2012 Elsevier Ltd. All rights reserved.