8-甲氧基-3-(4-硝基苯基)-2H-色烯-2-酮 | 1729-03-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 8-甲氧基-3-(4-硝基苯基)-2H-色烯-2-酮
• 英文名称: 8-methoxy-3-(4-nitrophenyl)-2H-chromen-2-one
• 英文别名: 8-methoxy-3-(4-nitrophenyl)coumarin；8-methoxy-3-(4-nitro-phenyl)-chromen-2-one；3-<4-Nitro-phenyl>-8-methoxy-cumarin；8-Methoxy-4'-nitro-3-phenyl-cumarin；8-methoxy-3-(4-nitrophenyl)chromen-2-one
• CAS: 1729-03-9
• 化学式: C₁₆H₁₁NO₅
• mdl: MFCD00582530
• 分子量: 297.267
• InChiKey: UEQZBWZNEQUUQA-UHFFFAOYSA-N

物化性质

• 熔点：
  >280 °C
• 沸点：
  528.4±50.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-甲氧基-3-(4-硝基苯基)-2H-色烯-2-酮 在 1,10-菲罗啉 、 copper(l) chloride 、 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以45%的产率得到7-methoxy-2-(4-nitrophenyl)benzo[b]furan
  参考文献：
  名称：

  Copper-catalyzed decarboxylative intramolecular C–O coupling: synthesis of 2-arylbenzofuran from 3-arylcoumarin

  摘要：

  建立了一种铜催化的脱羧分子内 CâO 偶联反应。在氯化铜/1,10-菲罗啉存在的有氧条件下，以 3-芳基香豆素为原料一锅制备了多种 2-芳基苯并呋喃，收率从 26% 到 84%不等。

  DOI：

  10.1039/c3ra46414h
• 作为产物：
  描述：

  8-methoxy-3-(4-nitrophenyl)iminocoumarin 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以53%的产率得到8-甲氧基-3-(4-硝基苯基)-2H-色烯-2-酮
  参考文献：
  名称：

  通过振动光谱和 DFT 计算研究水解和取代对香豆素衍生物光学性质的影响

  摘要：

  摘要 已成功合成了一系列香豆素衍生物。所有化合物均已通过 IR 和拉曼振动光谱技术在固态水平上进行表征。在固体薄膜上进行光吸收和光致发光测量。所有化合物都显示出吸收带，包括 π-π* 和 n-π* 电子跃迁以及蓝绿色光谱范围内的强发射。已经注意到大的斯托克斯位移并且可以解释即使在环境温度下的发光稳定性。我们主要对水解和第 8 位的甲氧基取代影响使用实验结果和理论计算的光学性质感兴趣。讨论表明，通过调整间隙能量和斯托克斯位移的增强，吸收和发射光谱的最大值受到影响和移动。有人注意到实验结果和理论结果之间有很好的一致性。

  DOI：

  10.1016/j.molstruc.2018.05.012

文献信息

• Coumarins: Fast Synthesis by Knoevenagel Condensation under Microwave Irradiation
  作者：Dariusz Bogdał

  DOI：10.1039/a801724g

  日期：——

  Condensation of salicyaldehyde or its derivatives with various derivatives of ethyl acetate in the presence of piperidine leads to the synthesis of coumarins by a solvent free reaction under microwave irradiation.

  在哌啶的存在下，水杨醛或其衍生物与各种乙酸乙酯衍生物的缩合导致在微波辐射下通过无溶剂反应合成香豆素。
• Structure-Based Optimization of Coumarin hA₃ Adenosine Receptor Antagonists
  作者：Maria João Matos、Santiago Vilar、Saleta Vazquez-Rodriguez、Sonja Kachler、Karl-Norbert Klotz、Michela Buccioni、Giovanna Delogu、Lourdes Santana、Eugenio Uriarte、Fernanda Borges

  DOI：10.1021/acs.jmedchem.9b01572

  日期：2020.3.12

  Adenosine receptors participate in many physiological functions. Molecules that may selectively interact with one of the receptors are favorable multifunctional chemical entities to treat or decelerate the evolution of different diseases. 3-Arylcoumarins have already been studied as neuroprotective agents by our group. Here, differently 8-substituted 3-arylcoumarins are complementarily studied as ligands of adenosine receptors, performing radioligand binding assays. Among the synthesized compounds, selective A(3) receptor antagonists were found. 3-(4-Bromophenyl)-8-hydroxycoumarin (compound 4) displayed the highest potency and selectivity as A(3) receptor antagonist (K-i = 258 nM). An analysis of its X-ray diffraction provided detailed information on its structure. Further evaluation of a selected series of compounds indicated that it is the nature and position of the substituents that determine their activity and selectivity. Theoretical modeling calculations corroborate and explain the experimental data, suggesting this novel scaffold can be involved in the generation of candidates as multitarget drugs.
• Synthesis and Evaluation of Coumarin–Resveratrol Hybrids as 15-Lipoxygenaze Inhibitors
  作者：Samira Rahmani-Nezhad、Leila Khosravani、Mina Saeedi、Kouros Divsalar、Loghman Firoozpour、Yaghoub Pourshojaei、Yaghoub Sarrafi、Hamid Nadri、Alireza Moradi、Mohammad Mahdavi、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1080/00397911.2014.979947

  日期：2015.3.19

  A series of coumarin-resveratrol hybrids, 3-arylcoumarin derivatives 3a-u, were synthesized through the intermolecular condensation reaction of various salicylaldehydes and phenylacetic acids in the presence of 1,4-diazabicyclo[2.2.2]octane under solvent-free conditions. All the synthesized compounds were screened for their inhibitory potency against soybean 15-lipoxygenase. Among them, three compounds (3c, 3j, and 3q) showed good enzyme-inhibitory activities.
• ——
  作者：M. P. Nemeryuk、V. D. Dimitrova、A. L. Sedov、O. S. Anisimova、V. F. Traven'

  DOI：10.1023/a:1015359830129

  日期：——
• Synthesis, Molecular Modeling and Cytotoxicity Study of New 3-Phenyl Coumarin Derivatives against in vitro Cell Lines
  作者：Anuruddha Chabukswar、Prajakta V. Adsule、Swati Jagdale、Dishank V. Purandare、Kunal Raut、Yash Kale

  DOI：10.14233/ajchem.2024.31269

  日期：——

  In pursuit of more effective cancer treatments, researchers embarked on a study to enhance the coumarin derivative’s therapeutic potential. These compounds, known for their anticancer properties, have faced challenges such as increased toxicity and drug resistance. The research aimed to design, synthesize and assess new 3-phenyl coumarin derivatives specifically for breast and lung cancer treatment. Utilizing 3-oxoacyl-reductase (1T8I), a series of compounds were synthesized from aromatic aldehydes and phenylacetic acid. Among the synthesized 11 compounds that were examined, compounds C01, C04, C05 and C08 had significant cytotoxic effects on both MCF-7 and MRC-5 cell lines. Particularly, compound C08, featuring ethoxy and nitrate substitution, exhibited remarkable potential against both cancer cell lines, emphasizing its promise for further exploration in cancer therapy.