2-amino-4-(2-oxo-2-phenylethyl)-4H-chromene-3-carbonitrile | 1428871-71-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-4-(2-oxo-2-phenylethyl)-4H-chromene-3-carbonitrile
• 英文别名: 2-Amino-4-(2-oxo-2-phenylethyl)-4h-chromene-3-carbonitrile；2-amino-4-phenacyl-4H-chromene-3-carbonitrile
• CAS: 1428871-71-9
• 化学式: C₁₈H₁₄N₂O₂
• 分子量: 290.321
• InChiKey: IOPNHJNVGRHMKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  水杨醛 在 铜色树碱 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 72.0h， 生成 2-amino-4-(2-oxo-2-phenylethyl)-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Enantioselective synthesis of 2-amino-3-nitrile-chromenes catalyzed by cinchona alkaloids: A remarkable additive effect

  摘要：

  2-Amino-3-nitrile-chromenes with potential antitumor activity were constructed by a novel catalytic system. In combination with alpha-naphthol, quinine could effectively promote the Michael-cyclization process of malononitrile with functionalized chalcones in high yields and moderate to good enantioselectivity (up to 84% ee). It is notable that the enantioselectivity could be greatly improved when a-naphthol was employed as additive. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.08.013

文献信息

• Exploitation of new chalcones and 4H-chromenes as agents for cancer treatment
  作者：Olívia Pontes、Marta Costa、Filipa Santos、Belém Sampaio-Marques、Tatiana Dias、Paula Ludovico、Fátima Baltazar、Fernanda Proença

  DOI：10.1016/j.ejmech.2018.07.058

  日期：2018.9

  Chalcone and chromene derivatives were synthesized in good yield through simple and effective reactions using innocuous solvents such as water and ethanol and high yielding aldol condensations. Generally, the reactions were performed at room temperature, leading to the isolation of highly pure compounds. These compounds were tested on breast cancer cells (MCF-7 and Hs578T) and breast non-neoplastic

  查尔酮和色烯衍生物是通过使用无毒溶剂（例如水和乙醇）和高产率的醛醇缩合进行的简单有效的反应以高收率合成的。通常，反应在室温下进行，从而导致高纯度化合物的分离。在乳腺癌细胞（MCF-7和Hs578T）和乳腺癌非肿瘤细胞（MCF-10A）上测试了这些化合物。测定IC 50之后值，进行了专门的分析以分析这些化合物的潜力，与甲氧基或甲基相比，那些带有卤代取代基的化合物具有增强的活性。更具体地说，溴原子通常存在于进行最终测定的生物活性分子中，并被证明是有希望进行进一步研究的候选物。所选色烯充当细胞迁移抑制剂，并触发与G 2 / M细胞逮捕和微管失稳相关的受调控的细胞死亡。对于查耳酮，结果表明具有抗增殖活性。同样，联合疗法的结果增强了阿霉素的抗肿瘤作用并降低了MCF-10A细胞的细胞毒性。
• An unusual and facile N-hetero cyclisation of 2-amino-4-(2-oxo-2-arylethyl)-4H-chromene-3-carbonitrile derivatives using hypervalent iodine in alcohol under ambient condition
  作者：Sourav Mal、Manoranjan Jana

  DOI：10.1016/j.tetlet.2020.152355

  日期：2020.10

  A very important functionalized benzopyran moiety has been further functionalized along with an unusual N-heterocyclic ring formation in a single step under ambient condition in room temperature under the influence of hypervalent iodine to produce a structurally interesting motif which can have some interesting biological properties having a similar but modified structure as that of bio-active chromene moieties. (C) 2020 Elsevier Ltd. All rights reserved.
• Facile and straightforward synthesis of the racemic version of 2-amino-4H-chromene-3-carbonitriles using K2HPO4 as an eco-friendly base
  作者：Sourav Mal、Manoranjan Jana

  DOI：10.1016/j.jics.2021.100202

  日期：2021.11
• Selective Synthesis of Cyano-Functionalized 2-Aryl-4H-chromenes and 2-Amino-4H-chromene-3-carbonitriles by Catalyst-Tuned Reactions of 2-Hydroxychalcones with 2-Substituted Acetonitriles
  作者：Guodong Yin、Houqiang Shi、Liqianyun Xu、Xianhong Wei、Qing Tao

  DOI：10.1055/s-0032-1317945

  日期：——

  A selective synthesis of 4H-chromenes by the reactions of 2-hydroxychalcone derivatives with acetonitriles substituted with electron-withdrawing groups is described. Under catalyst-free conditions, the reactions give cyano-functionalized 2-aryl-4H-chromenes, whereas in the presence of sodium bicarbonate, 2-amino-4H-chromene-3-carbonitriles are obtained in excellent yields.
• Enantioselective synthesis of 2-amino-3-nitrile-chromenes catalyzed by cinchona alkaloids: A remarkable additive effect
  作者：Yuan-Qin Zheng、Chun-Feng Luan、Zhi-Jing Wang、Yong-Qi Yao、Zhi-Chuan Shi、Xue-Feng Li、Zhi-Gang Zhao、Feng Chen

  DOI：10.1016/j.cclet.2015.08.013

  日期：2016.1

  2-Amino-3-nitrile-chromenes with potential antitumor activity were constructed by a novel catalytic system. In combination with alpha-naphthol, quinine could effectively promote the Michael-cyclization process of malononitrile with functionalized chalcones in high yields and moderate to good enantioselectivity (up to 84% ee). It is notable that the enantioselectivity could be greatly improved when a-naphthol was employed as additive. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.