3-(3-(4-hydroxy-3-methoxyphenyl)acryloyl)-2H-chromen-2-one | 91527-64-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(3-(4-hydroxy-3-methoxyphenyl)acryloyl)-2H-chromen-2-one
• 英文别名: 3-[3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoyl]chromen-2-one；3-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]chromen-2-one
• CAS: 91527-64-9
• 化学式: C₁₉H₁₄O₅
• 分子量: 322.317
• InChiKey: MVWKZSQWYQTEPE-UHFFFAOYSA-N

物化性质

• 熔点：
  212-214 °C
• 沸点：
  562.8±50.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3-(4-hydroxy-3-methoxyphenyl)acryloyl)-2H-chromen-2-one 在 吡啶 、 ammonium acetate 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 17.0h， 生成 2-methoxy-4-(2-methyl-4-oxo-7-(2-oxo-2H-chromen-3-yl)-3,4-dihydropyrido[2,3-d]pyrimidin-5-yl)phenyl acetate
  参考文献：
  名称：

  具有预期抗菌活性的新型香豆素衍生物的便捷合成

  摘要：

  Chalcone and coumarin are two substantial classes of natural products possessing significant antimicrobial activities. Hybrid compounds containing both structures have been synthesized in a good yield using Claisen-Schmidt aldolic condensation. The reaction of the new chalcones with active methylene compounds under different reaction conditions led to the construction of pyridine, pyran, pyrazole and pyridinone containing coumarin moiety with different functional groups. Investigating the antimicrobial activity of the new synthesized heterocycles, displays that 3-(2'-amino-3'-cyano-4'-(4-hydroxy-3-methoxyphenyly)pyrid-6'-yl)-coumarin 2a has the highest antimicrobial activity toward both Gram-positive and Gram-negative bacteria. Consequently, it was utilized as starting material for synthesis of more new fused heterocycles with anticipated high biological activity. All the new compounds are well characterized using, elemental analysis, FT-IR, H-1 NMR, ESI-Mass Spectrum and tested for their antimicrobial activity.

  DOI：

  10.3987/com-17-13779
• 作为产物：
  描述：

  水杨醛 在 哌啶 作用下， 以 氯仿 为溶剂， 反应 1.5h， 生成 3-(3-(4-hydroxy-3-methoxyphenyl)acryloyl)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Novel Series of 1,3-Dicoumarinyl-5-aryl-2-pyrazolines

  摘要：

  In the present paper novel 1,3,5-trisubstituted 2-pyrazolines (4a-q) were synthesized via condensation of different substituted 3-cinnamoyl-2-oxo-2H-chromenes (2a-q) with 2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetohydrazide (3). Chalcones were prepared via Claisen-Schmidt condensation by refluxing 3-acetyl-2-oxo-2H-chromen (1) with corresponding aldehydes in ethanol, in the presence of piperidine. All of these compounds were characterized by means of their IR, (1)H NMR and LC/MS/MS spectroscopic data and elemental microanalysis. Chalcones and pyrazolines were screened for their antioxidant and iron chelating activity.

  DOI：

  10.3987/com-11-12196

文献信息

• Microwave-assisted synthesis and evaluation of antimicrobial activity of 3-{3-(s-aryl and s-heteroaromatic)acryloyl}-2<i>H</i>-chromen-2-one derivatives
  作者：Olayinka O. Ajani、Obinna C. Nwinyi

  DOI：10.1002/jhet.298

  日期：——

  analytical and spectral data. All the synthesized compounds were screened for their antibacterial activity and 3-3-(4-dimethylaminophenyl)acryloyl}-2H-chromen-2-one () was discovered to be the most active at minimum inhibitory concentration (MIC) value of 7.8 μg/mL. J. Heterocyclic Chem., (2010).

  在本文中，利用缩合反应的方法对微波作为杂环合成能源的潜在利用进行了探索。3-乙酰香豆素（）与芳族和杂芳族醛形成相应的芳族查耳酮（）和杂芳族查耳酮（ 和 ）分别在1-3分钟内达到良好或优异的产量。化学结构通过分析和光谱数据证实。所有合成的化合物筛选它们的抗菌活性和3- 3-（4-二甲基氨基苯基）丙烯酰基} -2- ħ -色烯-2-酮（发现）在7.8μg/ mL的最小抑菌浓度（MIC）值下活性最高。J.杂环化​​学。（2010）。
• Design, synthesis and anticancer screening of 3-(3-(substituted phenyl) acryloyl)-2H-chromen-2ones as selective anti-breast cancer agent
  作者：Santosh N. Mokale、Afreen Begum、Nikhil S. Sakle、Vishakha R. Shelke、Swati A. Bhavale

  DOI：10.1016/j.biopha.2017.02.089

  日期：2017.5

  By utilizing concept of molecular hybridization, involving combination of various Pharmacophore, novel substituted coumarin-chalcone hybrids was synthesized and evaluated for anti-proliferative activity against estrogen receptor-positive MCF-7 and negative MDA-MB-435 breast cancer cell lines. In-vivo study was carried out by N-methyl nitrosourea (MNU) induced mammary carcinoma in virgin female Spraque

  通过利用分子杂交的概念，涉及各种药理学的组合，合成了新型取代的香豆素-查耳酮杂种，并评估了其对雌激素受体阳性的MCF-7和阴性的MDA-MB-435乳腺癌细胞系的抗增殖活性。体内研究是由N-甲基亚硝基脲（MNU）诱导的处女雌性Spraque Dawly（SD）大鼠的乳腺癌。与标准药物阿霉素相比，化合物5b具有最高的潜力，与他莫昔芬对ER阳性MCF-7乳腺癌细胞系相当。进行对接研究以研究合成化合物对ER-α酶的结合方向和亲和力。
• Spectral, thermal, biological and multi-heating rate kinetic properties of Cu(II) complexes containing N₂O₂donor ligands: 1,10-phenanthroline and acyl coumarins
  作者：Jiten C. Patel、Hitesh R. Dholariya、Ketan S. Patel、Kanuprasad D. Patel

  DOI：10.1002/aoc.2907

  日期：2012.11

  A series of newly synthesized coumarin‐based mixed‐ligand copper complexes with 1,10‐phenanthroline (Ph) were investigated by means of thermogravimetry, differential thermogravimetry, differential scanning calorimetry (DSC), electronic spectra and magnetic measurements. Structural and spectroscopic properties of neutral bidentate ligands as well as all complexes were studied on the basis of mass spectra

  通过热重分析，差示热重分析，差示扫描量热法（DSC），电子光谱和磁测量研究了一系列新合成的具有1,10-菲咯啉（Ph）的香豆素基混合配体铜配合物。在质谱，NMR（1 H和13 C）光谱，FT-IR分光光度法和元素分析的基础上，研究了中性双齿配体以及所有配合物的结构和光谱性质。红外光谱数据表明配体与金属离子的四配位N 2 O 2键。在不同的加热速率下（2.5–20°C min -1，对铜络合物进行DSC实验的动态扫描）。使用基辛格和小泽的等值转换方法确定指数前因子（A），活化能（E a）和反应阶数（n）。通过基辛格和小泽的方法获得的第二步降解动力学参数非常吻合。结果表明，络合物比配体具有更强的自由基清除剂和抗氧化剂化合物。配体及其铜化合物对结核分枝杆菌的抗分枝杆菌筛选显示，在铜络合后，抗结核活性明显增强。该配合物对枯草芽孢杆菌，金黄色葡萄球菌，与它的游离配体相比，已经发现了大肠杆菌，伤寒沙门
• Synthesis, spectroscopic, thermal and biological aspect of mixed ligand copper(II) complexes
  作者：G. J. Kharadi、K. D. Patel

  DOI：10.1007/s10973-009-0038-z

  日期：2009.6

  coordinating ability towards metal ion such as Copper(II). The structure of mixed ligand complexes has been investigated using spectral, elemental and thermal analysis. In vitro anti microbial activity against four bacterial species were performed i.e. Escherichia coli, Pseudomonas aeruginosa, Serratia marcescens, Bacillus substilis and found that synthesized complexes (15–37 mm) were found to be significant

  8-羟基喹啉的衍生物，即氯喹诺醇，以其抗生素特性，药物设计和对铜（II）等金属离子的配位能力而闻名。混合配体配合物的结构已使用光谱，元素和热分析进行了研究。对四种细菌进行了体外抗微生物活性，即大肠杆菌，铜绿假单胞菌，粘质沙雷氏菌，枯草芽孢杆菌，发现合成的复合物（15-37 mm）与标准药物（氯喹诺醇，即10-26）相比具有显着的效力。 （mm），用于配位的亲本配体和金属盐。动力学参数，例如反应顺序（n = 0.96-1.49）和活化能（E a  = 3.065–142.9 kJ mol -1）已使用Freeman–Carroll方法计算。发现前指数因子（A），活化熵（S * = −91.03至−102.6 JK -1  mol -1），活化焓（H * = 0.380–135.15 kJ mol -1）和活化的自由能（G * = 33.52–222.4 kJ mol -1）表明，络合物更稳定。发现配合物的稳定性顺序为[Cu（A
• Liu, Manman; Liu, Qian; Zhang, Jian, Journal of the Chemical Society of Pakistan, 2016, vol. 38, # 2, p. 301 - 306
  作者：Liu, Manman、Liu, Qian、Zhang, Jian

  DOI：——

  日期：——