11-amino-12-(3,4,5-trimethoxyphenyl)-8,9,10,12-tetrahydro-7H-chromeno[2,3-b]quinolin-3-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 11-amino-12-(3,4,5-trimethoxyphenyl)-8,9,10,12-tetrahydro-7H-chromeno[2,3-b]quinolin-3-ol
• 英文别名: 2-amino-4-(3,4,5-trimethoxy)phenyl-7-hydroxy-4H-chromene-3-carbonitrile；2-amino-7-hydroxy-4-(3,4,5-trimethoxyphenyl)-4H-chromene-3-carbonitrile；amino-7-hydroxy-4-(3,4,5-trimethoxyphenyl)-4H-chromene-3-carbonitrile；2-amino-3-cyano-7-hydroxy-4-(3,4,5-trimethoxyphenyl)-4H-chromene
• 化学式: C₁₉H₁₈N₂O₅
• 分子量: 354.362
• InChiKey: TWSVURCWPHWPRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  11-amino-12-(3,4,5-trimethoxyphenyl)-8,9,10,12-tetrahydro-7H-chromeno[2,3-b]quinolin-3-ol 在 五氧化二碘 、 水 、 溶剂黄146 作用下， 反应 0.33h， 以73%的产率得到7-hydroxy-2-oxo-4-(3,4,5-trimethoxyphenyl)-2H-chromene-3-carbonitrile
  参考文献：
  名称：

  New approach to synthesis of 4-arylcoumarin derivatives

  摘要：

  A simple and highly efficient new approach for the synthesis of 4-aryl-2-oxo-2H-chromene-3-carbonitriles based on the oxidation and hydrolysis of 2-amino-4-aryl-4H-chromene-3-carbonitriles is described. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.09.111
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 哌啶 作用下， 以 丙醇 为溶剂， 反应 0.08h， 生成 11-amino-12-(3,4,5-trimethoxyphenyl)-8,9,10,12-tetrahydro-7H-chromeno[2,3-b]quinolin-3-ol
  参考文献：
  名称：

  Synthesis and anti-inflammatory activities of 4H-chromene and chromeno[2,3-b]pyridine derivatives

  摘要：

  在微波辐照下，通过一锅反应高效地制备了几种 4H-色烯和色烯并[2,3-b]吡啶的衍生物，并评估了它们的抗炎活性。与槲皮素相比，六种合成产物（1b、1c、1h、2d、2j 和 2l）能更有效地抑制肿瘤坏死因子-α 诱导的一氧化氮（NO）的产生，并在人和猪软骨细胞中表现出相当的细胞活力。特别是，剂量为 10 和 20 毫克/千克的 2d 具有非常强的抗炎作用，能抑制角叉菜胶诱导的大鼠爪水肿和前列腺素 E2 的形成。本文的研究结果表明，这些化合物有可能成为设计和开发新型抗炎药物的结构模板。

  DOI：

  10.1007/s11164-015-2081-7

文献信息

• Substituted 4H-chromenes and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cytovia, Inc.

  公开号：US20030065018A1

  公开（公告）日：2003-04-03

  The present invention is directed to substituted 4H-chromenes and analogs thereof, represented by the general Formula I: 1 wherein R 1 -R 5 , A, Y and Z are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及被一般式I表示的取代的4H-香豆素及其类似物： 1 其中R 1 -R 5 ，A，Y和Z在此处被定义。本发明还涉及发现具有式I的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于诱导在各种临床病况中发生细胞死亡，其中异常细胞的不受控制的生长和传播。
• An expeditious synthesis of novel pyranopyridine derivatives involving chromenes under controlled microwave irradiation
  作者：Dushyant Singh Raghuvanshi、Krishna Nand Singh

  DOI：10.3998/ark.5550190.0011.a25

  日期：——

  An efficient synthesis of novel pyrano[2,3-b]pyridine derivatives has been achieved by the cyclocondensation of 2-amino-3-cyano-4H-chromenes and cyclohexanone in the presence of aluminium chloride under controlled microwave irradiation. The experimental conditions have been thoroughly optimized and established, allowing significant rate enhancements and excellent yields. The starting 4H-chromenes were

  2-氨基-3-氰基-4H-色烯和环己酮在氯化铝存在下，在受控的微波辐射下进行环缩合反应，实现了新型吡喃并[2,3-b]吡啶衍生物的有效合成。实验条件已经过彻底优化和建立，可以显着提高速率和优异的产量。使用一锅 DBU 催化的微波诱导间苯二酚、丙二腈和芳香醛的多组分缩合获得起始 4H-色烯。
• Aqua-mediated multicomponent synthesis of various 4H-pyran derivatives catalyzed by poly(4-vinylpyridine)-supported copper iodide nanoparticle catalyst
  作者：Jalal Albadi、Azam Mansournezhad

  DOI：10.1007/s11164-015-2400-z

  日期：2016.6

  A green and efficient approach for synthesis of some new 4 H -pyran derivatives is reported, catalyzed by green recyclable poly(4-vinylpyridine)-supported copper iodide nanoparticle catalyst in water. This procedure has many advantages such as operational simplicity, short reaction time, clean procedure, and high product yield.

  报道了一种绿色高效合成一些新的4 H- 吡喃衍生物的方法，该方法由绿色可回收的聚（4-乙烯基吡啶）负载的碘化铜纳米粒子催化剂在水中催化。该过程具有许多优点，例如操作简单，反应时间短，清洁过程和高产物产率。
• A green route towards substituted 2-amino-4H-chromenes catalyzed by an organobase (TBD) functionalized mesoporous silica nanoparticle without heating
  作者：Bikash Karmakar、Rajesh Nandi

  DOI：10.1007/s11164-016-2755-9

  日期：2021.5

  1,5,7-Triazabicyclo-[4,4,0]-dec-1-ene functionalized mesoporous silica nanoparticle promoted one-pot multicomponent synthesis of 2-amino-4H-chromenes from a phenolic component, different aldehydes and malononitrile was achieved in aqueous media at room temperature. The methodology promises advantages of short reaction times, environmentally benign conditions, high yields, and operational convenience

  1,5,7-三氮杂双环-[4,4,0]-癸-1-烯官能化的介孔二氧化硅纳米粒子促进了酚类，不同醛和丙二腈单锅多组分合成2-氨基-4 H-色烯的过程。在室温下在水性介质中达到的效果。该方法具有反应时间短，对环境有益的条件，高收率和操作方便的优点。催化剂被重复使用了几次，而活性没有明显损失。
• SUBSTITUTED 4H-CHROMENES AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS AND THE USE THEREOF
  申请人：Cai Xiong Sui

  公开号：US20060035925A1

  公开（公告）日：2006-02-16

  The present invention is directed to substituted 4H-chromenes and analogs thereof, represented by the general Formula I: wherein R 1 -R 5 , A, Y and Z are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及代替的4H-香豆素及其类似物，由通式I表示：其中R1-R5，A，Y和Z在此定义。本发明还涉及发现具有通式I的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于诱导在各种临床情况下不受控制的异常细胞的生长和扩散引起的细胞死亡。