(E)-1-(4-aminophenyl)-3-(4-nitrophenyl)prop-2-en-1-one | 569646-62-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(4-aminophenyl)-3-(4-nitrophenyl)prop-2-en-1-one
• 英文别名: (2E)-1-(4-Aminophenyl)-3-(4-nitrophenyl)-prop-2-EN-1-one
• CAS: 569646-62-4
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: KYLCMFUFMXUFFW-XCVCLJGOSA-N

物化性质

• 熔点：
  221-223 °C
• 沸点：
  474.3±45.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-aminophenyl)-3-(4-nitrophenyl)prop-2-en-1-one 在 sodium phosphate dodecahydrate 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 (S,E)-2-((4-(3-(4-nitrophenyl)acryloyl)phenyl)amino)-2-oxoethyl (2-oxotetrahydrofuran-3-yl)carbamodithioate
  参考文献：
  名称：

  Discovery of novel AHLs as potent antiproliferative agents

  摘要：

  Three series of novel AHL analogs were synthesized and evaluated for their in vitro cytotoxic activity against four human cancer cell lines. The SARs investigation indicated that AHLs with a terminal phenyl group, especially those with the chalcone scaffold had remarkably enhanced cytotoxicity than those with the hydrophobic side chains. Besides, some of these compounds were much more potent than 5-Fu and natural OdDHL. Through the detailed SARs discussions, we found that compounds 10a-k and 14 with the 4-amino chalcone scaffold showed excellent inhibition against all the tested cancer cell lines and were much more potent than 5-Fu and AHLs. Such scaffold may act as a template for further lead optimization. Compound 10i with a 3, 4, 5-trimethoxy group was the most potent one against all the tested cancer cell lines. Flow cytometry analysis indicated that analog lie induced the cellular apoptosis and cell cycle arrest of MCF-7 cells at G2/M phase in a concentration-and time-dependent manner. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.026
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 生成 (E)-1-(4-aminophenyl)-3-(4-nitrophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Marrian; Russell; Todd, Journal of the Chemical Society, 1947, p. 1419

  摘要：

  DOI：

文献信息

• Design, synthesis and evaluation of chalcones as H1N1 Neuraminidase inhibitors
  作者：Anand S. Chintakrindi、Devanshi J. Gohil、Sweta T. Kothari、Abhay S. Chowdhary、Meena A. Kanyalkar

  DOI：10.1007/s00044-017-2124-2

  日期：2018.4

  A series of chalcone derivatives (1a–2i) were designed based on isoliquiritigenin (the most active natural chalcone non-competitive neuraminidase (NA) inhibitor). Molecular modeling studies revealed that isoliquiritigenin and its designed analogs occupied 430-loop cavity of NA and interacted favorably with catalytic site residues. The favorable derivatives were synthesized and evaluated for cytotoxicity

  基于异寡糖原蛋白（最活跃的天然查尔酮非竞争性神经氨酸酶（NA）抑制剂）设计了一系列查尔酮衍生物（1a – 2i）。分子模型研究表明，异寡糖原蛋白及其设计的类似物占据了NA的430环腔，并与催化位点残基相互作用。合成了有利的衍生物，并评价了其对H1N1病毒的细胞毒性和对细胞病变作用的抑制作用。通过血凝（HA）测定，H1N1-NA抑制和抑制动力学进一步量化了抑制作用。HA分析表明，化合物1e的最低EC 50为1.71 nM。相反，H1N1-NA抑制试验显示化合物1f具有3.58μM的IC 50最佳活性。酶动力学研究表明化合物1f和2f的抑制机理是非竞争性的。
• Synthesis, docking studies and<i>in vitro</i>evaluation of novel chalcones as potent inhibitors of phosphodiesterase 5 from human platelets and 5A from bovine recombinant
  作者：Amol S. Sherikar、Rakesh P. Dhavale、Manish S. Bhatia

  DOI：10.1039/c8nj02077a

  日期：——

  nitrate esters as the final product. The inhibitory potency of the synthesized compounds was evaluated against PDE 5 from human platelets and PDE 5A from bovine recombinant and compared with Tadalafil and a standard inhibitor. Compounds AI7, B5, B7, E7 and E8 containing acetyl, nitro, carboxy methyl, hydroxy methyl functionalities exhibit a marked inhibitory effect against human platelet PDE 5. Compounds

  合成了一系列新的一氧化氮供体查耳酮部分，并分别评估了来自人血浆和牛重组体的磷酸二酯酶5（PDE 5）和5A（PDE 5A）抑制潜力。分子对接显示合成的化合物与受体的极好的结合相互作用。查尔酮中间体i的合成是在克莱森-施密特缩合反应的基础上，通过使取代的醛与苯乙酮反应来进行的。进行硝化反应，得到以硝酸苯基酯和硝酸酯为最终产物的取代查尔酮。评价了合成化合物对人血小板中的PDE 5和牛重组体中的PDE 5A的抑制能力，并与他达拉非和标准抑制剂进行了比较。化合物含有乙酰基，硝基，羧甲基，羟甲基官能团的AI7，B5，B7，E7和E8对人血小板PDE 5表现出明显的抑制作用。化合物B2，B4，B5，D4，D6和E6含有硝基，氟，氨基，甲基官能团显示出对重组牛PDE 5A的显着抑制作用。在查尔酮上含有硝酸苯基部分和乙酰基官能团的化合物AI7对人血小板PDE 5的抑制能力为1.197±3.38μM。化合物
• Synthesis, Characterization and Molecular Docking of 1,2,4-Triazole Derivatives as Potential Antimicrobial Agents
  作者：Panneerselvam Kalaivani、Jayaraman Arikrishnan、Mannuthusamy Gopalakrishnan

  DOI：10.14233/ajchem.2020.22594

  日期：——

  In this study, a new series of (E)-N-(4-(3-(3,5-dialkylphenyl)acryloyl)phenyl)-2-(1H-1,2,4-triazol-1- yl)acetamide (32-41) was synthesized, characterized by FT-IR, 1H NMR, 13C NMR and Mass spectral analysis and evaluated for their in vitro antibacterial and antifungal activities. The docking study of the newly synthesized compounds was performed and results showed good binding mode in the active site of 1T9U protein. The zone of inhibition concentration was tested for the synthesized compounds against five bacterial and three fungal strains. Compounds 34 and 37 have good antibacterial activity. Compounds 3, 4 and 6 shows moderate inhibition against the antifungal activity.

  在这项研究中，合成了一系列新的(E)-N-(4-(3-(3,5-二烷基苯基)丙烯酰基)苯基)-2-(1H-1,2,4-三唑-1-基)乙酰胺（32-41），通过FT-IR、1H NMR、13C NMR和质谱分析进行表征，并评估了它们在体外抗菌和抗真菌活性。对新合成化合物进行了对接研究，结果显示这些化合物在1T9U蛋白的活性位点中有良好的结合模式。对合成化合物针对五种细菌和三种真菌菌株的抑菌浓度进行了测试。化合物34和37具有良好的抗菌活性。化合物3、4和6对抗真菌活性表现出中等抑制作用。
• Visible Light Activated Radical Denitrative Benzoylation of<i>β</i>-Nitrostyrenes: A Photocatalytic Approach to Chalcones
  作者：Shubhangi Tripathi、Ritu Kapoor、Lal Dhar S. Yadav

  DOI：10.1002/adsc.201701559

  日期：2018.4.3

  A metal‐free, convenient photocatalytic approach to chalcones from β‐nitrostyrenes and benzaldehydes via a radical denitrative benzoylation pathway is reported. The salient features of the protocol include the utilization of visible light as an inexpensive and ecosustainable energy source, N‐hydroxyphthalimide (NHPI) as a reusable organophotocatalyst and acetonitrile as an acceptable green solvent

  据报道，一种无金属，方便的光催化方法可通过自由基反硝化苯甲酰化途径从β-硝基苯乙烯和苯甲醛中分离出查耳酮。该协议的显着特征包括利用可见光作为一种廉价且生态可持续的能源，使用N-羟基邻苯二甲酰亚胺（NHPI）作为可重复使用的有机光催化剂，使用乙腈作为一种可接受的绿色溶剂，以在室温下以优异的产率提供查耳酮。锅程序。值得注意的是，这是β-硝基苯乙烯作为查尔酮合成的现成底物的首次应用，也是该领域中光催化的第一个实例。
• Synthesis, photophysical, voltammetric, and DFT studies of 4-aminochalones
  作者：Humera Baig、Rimsha Irfan、Alvina Rasool、Syed Zajif Hussain、Sabir Ali Siddique、Javed Iqbal、Meshari Alazmi、Nawaf Alshammari、Amira Alazmi、Amer AlGhadhban、Abdel Moneim E. Sulieman、Kamaleldin B. Said、Habib-ur- Rehman、Rahman Shah Zaib Saleem

  DOI：10.1016/j.jphotochem.2023.114790

  日期：2023.8

  −2.56, −2.99 respectively with band gap energy values 2.54–2.61 eV. The DFT and TD-DFT computations at the B3LYP functional along with a 6-31G(d,p) basis set for a comprehensive study of spectral data, molecular orbitals (HOMO, LUMO) analysis, and electrostatic potential (MEP) surfaces are also presented. The Computational studies support the experimental findings. The findings hint towards the optoelectronic

  使用 Claisen-Schmidt 缩合合成具有 DAD 结构的氨基查耳酮。通过 FTIR、熔点、HRMS、1 H 和13 C NMR 光谱对化合物进行了表征，并在不同溶剂（氯仿、乙腈和甲醇）中分析了紫外-可见光和荧光。所有化合物均在 330–420 nm 范围内显示吸收，在 400–550 nm 范围内显示发射。由于分子内电荷转移 (ICT) 相互作用，吸收和发射光谱都表现出从非极性溶剂到极性溶剂的红移。化合物17和18在极性溶剂中表现出巨大的斯托克斯位移 (Δλ = 116–130 nm)，使这些化合物具有更高的荧光特性。此外，化合物的 HOMO-LUMO 能级通过循环伏安法评估的17和18分别为 -5.10、-5.15 和 -2.56、-2.99，带隙能量值为 2.54-2.61 eV。B3LYP 泛函的 DFT 和 TD-DFT 计算以及用于光谱数据、分子轨道（HOMO、LUMO