7-(diethylamino)-3-(3-phenylacryloyl)coumarin | 77819-83-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-(diethylamino)-3-(3-phenylacryloyl)coumarin
• 英文别名: 3-cinnamoyl-7-(diethylamino)-2H-chromen-2-one；2H-1-Benzopyran-2-one, 7-(diethylamino)-3-(1-oxo-3-phenyl-2-propenyl)-；7-(diethylamino)-3-(3-phenylprop-2-enoyl)chromen-2-one
• CAS: 77819-83-1
• 化学式: C₂₂H₂₁NO₃
• 分子量: 347.414
• InChiKey: YCHOUXDNWWZEFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(diethylamino)-3-(3-phenylacryloyl)coumarin 在 肼 作用下， 生成 7-(diethylamino)-3-(5-phenyl-4, 5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one
  参考文献：
  名称：

  Designing novel inhibitors against falcipain-2 of Plasmodium falciparum

  摘要：

  Coumarin containing pyrazoline derivatives have been synthesized and tested as inhibitors of in vitro development of a chloroquine-sensitive (MRC-02) and chloroquine-resistant (RKL-2) strain of Plasmodium falciparum and in vivo Plasmodium berghei malaria. Docking study was also done on cysteine protease falcipain-2 which showed that the binding pose of C-14 molecule and epoxysuccinate, inhibitor of falcipain-2, binds in the similar pattern. The most active antimalarial compound was 3-(1-benzoyl-5-(4-flurophenyl)-4,5-dihydro-1H-pyrazol-3yl)-7-(diethyamino)-2H-chromen-2- one C-14, with an IC50 of 4.21 mu g/ml provided complete protection to the infected mice at 24 mg/kg X 4 days respectively. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.03.058
• 作为产物：
  描述：

  4-(二乙氨基)水杨醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 8.5h， 生成 7-(diethylamino)-3-(3-phenylacryloyl)coumarin
  参考文献：
  名称：

  香豆素-查耳酮杂化物的合成及荧光特性

  摘要：

  利用乙酰香豆素分别与三种苯甲醛和肉桂醛缩合合成了四种香豆素-查耳酮杂化物。此外，还测量了这些合成化合物在二氯甲烷中的吸收光谱和荧光光谱。

  DOI：

  10.3184/174751917x15035711817504

文献信息

• Synthesis and Fluorescent Properties of Coumarin–Chalcone Hybrids
  作者：Fang Yang、Hongli Fan、Ziyan Xue、Xiaolong Wang

  DOI：10.3184/174751917x15035711817504

  日期：2017.9

  Four coumarin–chalcone hybrids were synthesised utilising condensation of acetylcoumarin with three benzaldehydes and cinnamaldehyde, respectively. Moreover, the absorption and fluorescence spectra of these synthesised compounds in dichloromethane were measured.

  利用乙酰香豆素分别与三种苯甲醛和肉桂醛缩合合成了四种香豆素-查耳酮杂化物。此外，还测量了这些合成化合物在二氯甲烷中的吸收光谱和荧光光谱。
• The role of the intermolecular π···π interactions in the luminescence behavior of novel coumarin-based pyrazoline materials
  作者：V.F. Traven、D.A. Cheptsov、J.I. Svetlova、I.V. Ivanov、Cristián Cuerva、Carlos Lodeiro、Frederico Duarte、S.F. Dunaev、V.V. Chernyshev

  DOI：10.1016/j.dyepig.2020.108942

  日期：2021.2

  effects. The compound 1a molecules have π···π interactions proved by short distance of 3.61(2) Å between the centroids of six-membered cycles and weak intermolecular C–H…O hydrogen bonds, which link the π···π dimers into columns. According to quantum chemical calculations by TD DFT method with the B3LYP functional, in the def2-TZVP basis, intermolecular π···π interactions lead to strong red-shift (around

  合成了九种基于香豆素的吡唑啉并对其进行了全面表征，以寻找用于设计刺激响应性铬材料的新型荧光化合物。所有报告的化合物在溶液和固态下均表现为高荧光物质，分子间相互作用在其光物理性质中起关键作用。特别是化合物1a由于分子间π··π过渡的建立和/或破裂而表现出不可逆的热，机械，溶剂化和气相致变色行为，此外，由于添加了几种金属而形成的络合，其离子致变色性质盐。粉末XRD研究已经进行，以解释所述的刺激反应效应。化合物1a分子具有π··π相互作用，这是通过六元环的质心之间的短距离3.61（2）Å和弱的分子间C–H…O氢键来证明的，这些分子将π···π二聚体连接到列。根据具有B3LYP功能的TD DFT方法的量子化学计算，以def2-TZVP为基础，分子间π···π相互作用导致1a的电子吸收（EA）发生强烈的红移（约63 nm）。固态。相反，在2a结构中，没有任何有关π···π堆积的提示，并且从溶液到固态
• Discovery of a novel fluorescent HSP90 inhibitor and its anti-lung cancer effect
  作者：Su-Yun Bai、Xi Dai、Bao-Xiang Zhao、Jun-Ying Miao

  DOI：10.1039/c4ra01800a

  日期：——

  A novel fluorescent HSP90 inhibitor with strong growth inhibitory effects on lung cancer cells was developed.

  开发出一种新型荧光HSP90抑制剂，对肺癌细胞具有强烈的生长抑制作用。
• Fluorescence turn-on probe for biothiols: intramolecular hydrogen bonding effect on the Michael reaction
  作者：Hyun-Joon Ha、Doo-Ha Yoon、Seokan Park、Hae-Jo Kim

  DOI：10.1016/j.tet.2011.08.002

  日期：2011.10

  Weakly fluorescent coumarinyl enones are rapidly transformed into strongly fluorescent molecules through the Michael addition reaction of a thiol group, where an intramolecular hydrogen bond plays a critical role in the reaction rate. The molecular probe (3) with an ortho hydroxyl group to a carbonyl group exhibits a rapid response toward GSH owing to the stabilization of the possible oxyanion intermediate by a preferable intramolecular hydrogen bond. Probe 1 with an o-hydroxyl group also showed a moderately enhanced reaction rate with GSH and soluble in HEPES buffer to exhibit a highly selective and sensitive fluorescence turn-on response toward biothiols. (C) 2011 Elsevier Ltd. All rights reserved.
• Designing novel inhibitors against falcipain-2 of Plasmodium falciparum
  作者：Himangini、Dharam Pal Pathak、Vidushi Sharma、Sachin Kumar

  DOI：10.1016/j.bmcl.2018.03.058

  日期：2018.5

  Coumarin containing pyrazoline derivatives have been synthesized and tested as inhibitors of in vitro development of a chloroquine-sensitive (MRC-02) and chloroquine-resistant (RKL-2) strain of Plasmodium falciparum and in vivo Plasmodium berghei malaria. Docking study was also done on cysteine protease falcipain-2 which showed that the binding pose of C-14 molecule and epoxysuccinate, inhibitor of falcipain-2, binds in the similar pattern. The most active antimalarial compound was 3-(1-benzoyl-5-(4-flurophenyl)-4,5-dihydro-1H-pyrazol-3yl)-7-(diethyamino)-2H-chromen-2- one C-14, with an IC50 of 4.21 mu g/ml provided complete protection to the infected mice at 24 mg/kg X 4 days respectively. (C) 2018 Elsevier Ltd. All rights reserved.