methyl 2-(coumarin-4-yloxy)acetate | 936256-96-1

• 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: methyl 2-(coumarin-4-yloxy)acetate
• 英文别名: methyl 2-((2-oxo-2H-chromen-4-yl)oxy)acetate；Methyl 2-(2-oxo-2h-chromen-4-yloxy)acetate；methyl 2-(2-oxochromen-4-yl)oxyacetate
• CAS: 936256-96-1
• 化学式: C₁₂H₁₀O₅
• 分子量: 234.208
• InChiKey: WWIYBKOVQKEZMI-UHFFFAOYSA-N

物化性质

• 沸点：
  423.1±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(coumarin-4-yloxy)acetate 在 水 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以100%的产率得到2-[(2-oxo-2H-chromen-4-yl)oxy]acetic acid
  参考文献：
  名称：

  Novel Insect-Repellent Coumarin Derivatives, Syntheses, and Methods of Use

  摘要：

  本发明涉及新型香豆素衍生物、包含该衍生物的配方，以及制备和使用这些化合物和配方的方法，这些化合物和配方可作为驱虫剂防止昆虫和/或害虫。这些化合物还可以预防因昆虫/害虫传播的疾病和疾病，并提供比现有驱虫剂更安全、更有效的替代品。

  公开号：

  US20120329832A1
• 作为产物：
  描述：

  4-羟基香豆素 、 溴乙酸甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 10.0h， 以81%的产率得到methyl 2-(coumarin-4-yloxy)acetate
  参考文献：
  名称：

  4-羟基香豆素衍生物作为COX-II酶抑制剂的合成、抗炎作用、分子对接和分子动力学研究

  摘要：

  该研究旨在研究 4-羟基香豆素衍生物对大鼠炎症反应的抗炎作用，并评估所列化合物 (3-11) 在急性暴露后的毒性。通过以 10-3000 mg/kg 的规模向大鼠单独口服给药收集毒性报告，而在最后一次给药后的 10 天内观察到毒性迹象。使用二甲苯诱导的水肿模型和爪的角叉菜胶炎症模型估计对炎症的反应。 将化合物以每日一次的剂量口服给药至动物连续 7 天。使用COX-II酶进行分子对接研究，深入解释了合成化合物的活性。此外，计算机模拟结果与生物活性非常一致。有趣的是，化合物 5 和 10 显示出最高的结合点（较低的值）。因此，对活性最强的化合物 5 和 10 进行了分子动力学模拟研究。

  DOI：

  10.1016/j.molstruc.2021.131377

文献信息

• FUNCTIONALIZED PHENOLIC COMPOUNDS AND POLYMERS THEREFROM
  申请人：Bezwada Rao S.

  公开号：US20090170927A1

  公开（公告）日：2009-07-02

  The present invention relates to compounds of formula I, which are functionalized phenolic compounds, and polymers formed from the same. Ar—[O—(X) p —R′] q I Polymers formed from the functionalized phenolics are expected to have controllable degradation profiles, enabling them to release an active component over a desired time range. The polymers are also expected to be useful in a variety of medical applications.

  本发明涉及公式I的化合物，这些化合物是官能化酚类化合物，以及由它们形成的聚合物。从官能化酚类化合物形成的聚合物预计具有可控的降解特性，使它们能够在所需的时间范围内释放活性成分。这些聚合物还预计在各种医疗应用中有用。
• Synthesis and Characterization of Some New 4-Hydroxy-coumarin Derivatives
  作者：Yasameen Al-Majedy、Abdul Kadhum、Ahmed Al-Amiery、Abu Mohamad

  DOI：10.3390/molecules190811791

  日期：——

  Some novel coumarins were synthesized starting from 4-hydroxycoumarin and methyl bromoacetate. The structures of the newly obtained compounds were confirmed by elemental analysis, mass, IR and NMR spectra.

  从4-羟基香豆素和溴乙酸甲酯出发，合成了一系列新型香豆素。通过元素分析、质谱、红外光谱和核磁共振谱，确认了新得到化合物的结构。
• New Coumarin Derivative as an Eco-Friendly Inhibitor of Corrosion of Mild Steel in Acid Medium
  作者：Ahmed Al-Amiery、Yasameen Al-Majedy、Abdul Kadhum、Abu Mohamad

  DOI：10.3390/molecules20010366

  日期：——

  The anticorrosion ability of a synthesized coumarin, namely 2-(coumarin-4-yloxy)acetohydrazide (EFCI), for mild steel (MS) in 1 M hydrochloric acid solution has been studied using a weight loss method. The effect of temperature on the corrosion rate was investigated, and some thermodynamic parameters were calculated. The results indicated that inhibition efficiencies were enhanced with an increase in concentration of inhibitor and decreased with a rise in temperature. The IE value reaches 94.7% at the highest used concentration of the new eco-friendly inhibitor. The adsorption of inhibitor on MS surface was found to obey a Langmuir adsorption isotherm. Scanning electron microscopy (SEM) was performed on inhibited and uninhibited mild steel samples to characterize the surface. The Density Function theory (DFT) was employed for quantum-chemical calculations such as EHOMO (highest occupied molecular orbital energy), ELUMO (lowest unoccupied molecular orbital energy) and μ (dipole moment), and the obtained results were found to be consistent with the experimental findings. The synthesized inhibitor was characterized by Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR) spectroscopic studies.

  通过失重法研究了一种合成香豆素，即2-（香豆素-4-氧基）乙酰肼（EFCI），在1M盐酸溶液中对低碳钢（MS）的防腐蚀能力。研究了温度对腐蚀速率的影响，并计算了一些热力学参数。结果表明，随着抑制剂浓度的增加，抑制效率增强，随着温度的升高而降低。这种新型环保抑制剂的最高使用浓度下的IE值达到94.7%。发现抑制剂在MS表面的吸附符合朗缪尔吸附等温线。对抑制和未抑制的低碳钢样品进行了扫描电子显微镜（SEM）表征表面。使用密度泛函理论（DFT）进行了量子化学计算，如EHOMO（最高占据分子轨道能量）、ELUMO（最低未占据分子轨道能量）和μ（偶极矩），所得结果与实验发现一致。通过傅里叶变换红外（FTIR）和核磁共振（NMR）光谱研究，对该合成抑制剂进行了表征。
• Synthesis of new coumarins complemented by quantum chemical studies
  作者：Ahmed A. Al-Amiery、Yasameen K. Al-Majedy、Abdul Amir H. Kadhum、Abu Bakar Mohamad

  DOI：10.1007/s11164-015-2252-6

  日期：2016.4

  New coumarins, namely (E)-N′-(2-methylbenzylidene)-2-((2-oxo-2H-chromen-4-yl)oxy)acetohydrazide 4, N-(4-oxo-2-(o-tolyl)thiazolidin-3-yl)-2-((2-oxo-2H-chromen-4-yl)oxy)acetamide 5, and N-(4,7-dioxo-2-(o-tolyl)-1,3-oxazepin-3(2H,4H,7H)-yl)-2-((2-oxo-2H-chromen-4-yl)oxy)acetamide 6, were synthesized starting from 4-hydroxycoumarin and methyl bromoacetate. They were characterized by different spectroscopic techniques (FT-IR and NMR) and micro-elemental analysis (CHNS). Density Functional Theory calculations of the synthesized coumarins were performed using molecular structures with optimized geometries. Molecular orbital calculations have provided detail description of the orbitals, including spatial characteristics, nodal patterns, and the contributions of individual atoms.

  新合成的香豆素化合物，分别为(E)-N'-(2-甲基苄叉)-2-((2-氧-2H-色烯-4-基)氧)乙酰肼4、N-(4-氧-2-(邻甲苯基)噻唑烷-3-基)-2-((2-氧-2H-色烯-4-基)氧)乙酰胺5和N-(4,7-二氧-2-(邻甲苯基)-1,3-噁二环[3.2.1]辛-3(2H,4H,7H)-基)-2-((2-氧-2H-色烯-4-基)氧)乙酰胺6，均由4-羟基香豆素和溴乙酸甲酯为原料合成。这些化合物通过不同的光谱技术（FT-IR和NMR）以及微量元素分析（CHNS）进行了表征。利用具有优化几何结构的分子进行密度泛函理论计算，对合成的香豆素进行了密度泛函理论计算。分子轨道计算详细描述了轨道，包括空间特性、节点模式以及单个原子的贡献。
• 4-Oxycoumarinyl linked acetohydrazide Schiff bases as potent urease inhibitors
  作者：Fouzia Naz、Kanwal、Mehreen Latif、Uzma Salar、Khalid Mohammed Khan、Mariya al-Rashida、Irfan Ali、Basharat Ali、Muhammad Taha、Shahnaz Perveen

  DOI：10.1016/j.bioorg.2020.104365

  日期：2020.12

  Urease enzyme is responsible to catalyze the hydrolysis of urea into carbamate and ammonia. Then carbamate hydrolyzed to ammonia and carbon dioxide. Excess release of ammonia leads to increase pH in stomach that actually encourages the survival of Helicobacter pylori. H. pylori involves in various disorders most commonly peptic ulcer, pyelonephritis, hepatic coma, kidney stone formation, urolithiasis, and encephalopathy. Apart from many pharmacological properties, coumarin and Schiff bases are known to possess urease inhibitory activity. Therefore, these two pharmacologically important scaffolds are combined into single hybrid molecules to assess their potential as urease inhibitors. For this aim, N'-benzylidene-2-((2-oxo-2H-chromen-4-yl)oxy)acetohydrazide Schiff base derivatives 3-27 were synthesized by following a three step reaction strategy. Structures of all synthetic molecules were characterized by EI-MS, ¹H-, and ¹³C NMR spectroscopic techniques. All molecules were assessed for urease inhibitory activity and found to possess a varying degree of inhibitory potential in the range of IC₅₀ = 12.3 ± 0.69 to 88.8 ± 0.04 μM. Amongst the active analogs, compounds 7 (IC₅₀ = 16.2 ± 0.11 μM), 9 (IC₅₀ = 15.2 ± 0.14 μM), 10 (IC₅₀ = 12.3 ± 0.69 μM), 12 (IC₅₀ = 16.3 ± 0.45 μM), and 15 (IC₅₀ = 17.6 ± 0.28 μM) were identified as potent inhibitors compared to standard urea (IC₅₀ = 21.5 ± 0.47 μM). It is conferred from structure-activity relationship (SAR) that variation in inhibitory activity is due to different substitutions pattern on aryl ring. Moreover, molecular docking studies were carried out to understand the interactions of ligand with the active pocket of urease enzyme.