2-amino-4-(2,6-dichlorophenyl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile | 939658-30-7

• 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-4-(2,6-dichlorophenyl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile
• 英文别名: 2-amino-4-(2,6-dichlorophenyl)-5,10-dioxo-4H-benzo[g]chromene-3-carbonitrile
• CAS: 939658-30-7
• 化学式: C₂₀H₁₀Cl₂N₂O₃
• 分子量: 397.217
• InChiKey: LTZAAXKOFFRKFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 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：
  93.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-4-(2,6-dichlorophenyl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile 、 乙酸酐 在 硫酸 、 水 作用下， 反应 0.25h， 以76%的产率得到5-(2,6-dichlorophenyl)-2-methyl-3H-benzo[6,7]chromeno[2,3-d]pyrimidine-4,6,11(5H)-trione
  参考文献：
  名称：

  四环吡喃并[2,3-d]嘧啶的高效合成

  摘要：

  通过2-氨基-3-氰基-4- H-吡喃与乙酸酐与酸催化剂的反应合成了一系列吡喃并[2,3- d ]嘧啶衍生物。该方法由于反应时间短且易于后处理而非常有效，并且为构建四环吡喃并[2,3- d ]嘧啶骨架提供了有效而有前途的合成策略。确认了产品的X射线晶体结构，并提供了可能的机理。

  DOI：

  10.1002/jhet.2630
• 作为产物：
  描述：

  2,6-二氯苯甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 2-amino-4-(2,6-dichlorophenyl)-5,10-dioxo-5,10-dihydro-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

• Design, synthesis, and evaluation of 1,4-naphthoquinone-chromene hybrids as potential anti-K562 and A549 agents
  作者：Wen-Hui Zhang、Bo Zhang、Bo-Wen Pan、Xiong-Wei Liu、Zhi-Gang Yin、Yu-Zhou Zhuo、Chuan-wen Lei、Ying Zhou

  DOI：10.1039/d3nj05743g

  日期：——

  Two series of 1,4-naphthoquinone-chromone hybrids 4a (4aa–4ao) and 4b (4ba–4bq) were designed, synthesized and evaluated as antitumor agents.

  设计、合成并评估了两个系列的 1,4-萘醌-色酮混合物 4a（4aa-4ao）和 4b（4ba-4bq）作为抗肿瘤药物。
• A novel Cu(II) nanoparticles anchored on cyanuric chloride-attached magnetic nanocatalyst: A highly stable, recyclable and efficient nanocatalyst for the synthesis of chromene derivatives
  作者：Fatemeh Kalantari、Sobhan Rezayati、Maryam Manafi Moghadam、Ali Ramazani

  DOI：10.1016/j.inoche.2024.112371

  日期：2024.6

  As a novel core-shell magnetic nanocatalyst, a copper nanocatalyst, Cu(II)-Schiff base-TCT-APTES@SiO@FeO was successfully synthesized through the reaction of the cyanuric chloride grafted onto the core-shell magnetic nanocatalyst with Schiff base complex and finally treated with Cu(NO)·3HO. The noteworthy point is that the novel Schiff base separated by employing hydrazine with 2-pyridinecarboxaldehyde

  作为一种新型核壳磁性纳米催化剂，通过将氰尿酰氯接枝到核壳磁性纳米催化剂上与希夫碱配合物反应，成功合成了铜纳米催化剂Cu(II)-席夫碱-TCT-APTES@SiO@FeO最后用Cu(NO)·3HO处理。值得注意的是，合成了肼与2-吡啶甲醛分离的新型席夫碱，并通过简单的洗涤纯化，并通过FT-IR、H NMR和C NMR谱鉴定。该催化剂依靠各种技术和光谱程序进行了研究，包括 FT-IR、SEM、TEM、XPS、XRD、VSM、BET、TGA 和 ICP 分析。 TEM图像表明合成的催化剂平均尺寸为37-47 nm，形状为球形。 BET分析表明我们合成的催化剂具有介孔结构和高比表面积（52.55 m/g）。此外，XPS结果清楚地表明937.2 eV和949.2 eV处的峰与催化剂结构中Cu(II)的存在有关。然后，成功测试了铜纳米催化剂在乙醇中回流条件下，各种醛类、酚类（2-羟基萘-1,4-二酮
• 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.
• An Efficient Synthesis of Tetracyclic Pyrano[2,3-<i>d</i>]pyrimidines
  作者：Zhi-Lan Lin、Jun-Min Zhang、Yuan Gao

  DOI：10.1002/jhet.2630

  日期：2017.1

  A series of pyrano[2,3‐d]pyrimidine derivatives have been synthesized by the reaction of 2‐amino‐3‐cyano‐4H‐pyrans and acetic anhydride with acid catalyst . This method is very efficient because of short reaction times and easy work‐up, and it provides an efficient and promising synthetic strategy for the construction of the tetracyclic pyrano[2,3‐d]pyrimidine skeleton. The X‐ray crystal structures

  通过2-氨基-3-氰基-4- H-吡喃与乙酸酐与酸催化剂的反应合成了一系列吡喃并[2,3- d ]嘧啶衍生物。该方法由于反应时间短且易于后处理而非常有效，并且为构建四环吡喃并[2,3- d ]嘧啶骨架提供了有效而有前途的合成策略。确认了产品的X射线晶体结构，并提供了可能的机理。