2-(2-oxo-2H-chromen-4-yloxy)acetohydrazide | 669768-99-4

• 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: 2-(2-oxo-2H-chromen-4-yloxy)acetohydrazide
• 英文别名: 2-(coumarin-4-yloxy)acetohydrazide；2-(2-oxochromen-4-yl)oxyacetohydrazide
• CAS: 669768-99-4
• 化学式: C₁₁H₁₀N₂O₄
• 分子量: 234.211
• InChiKey: MNPJWEBGXCYAMW-UHFFFAOYSA-N

物化性质

• 熔点：
  227 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  571.8±50.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-oxo-2H-chromen-4-yloxy)acetohydrazide 以 苯 为溶剂， 反应 20.0h， 生成 N-[2-(4-amino-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-yl)4,7-dioxo-1,3-oxazepin-3(2H,4H,7H)-yl]-2-(coumarin-4-yloxy) acetamide
  参考文献：
  名称：

  Synthesis and Characterization of Some New 4-Hydroxy-coumarin Derivatives

  摘要：

  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。

  DOI：

  10.3390/molecules190811791
• 作为产物：
  描述：

  methyl 2-(coumarin-4-yloxy)acetate 在 hydrazine hydrate monohydrate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以57%的产率得到2-(2-oxo-2H-chromen-4-yloxy)acetohydrazide
  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

• Synthesis of Novel Quinolone and Coumarin Based 1,3,4-Thiadiazolyl and 1,3,4-Oxadiazolyl N-Mannich Bases as Potential Antimicrobials
  作者：Rahul V. Patel、Jigar K. Patel、Premlata Kumari、Kishor H. Chikhalia

  DOI：10.2174/157017812802139681

  日期：2012.7.1

  Two series of 1,3,4-thiadiazole and 1,3,4-oxadiazole derivatives have been synthesized and characterized by elemental and spectral (IR, 1H-NMR) data. The hydrazide derivatives of 4-hydroxy quinolone and coumarin moiety were refluxed in carbon disulfide in ethanolic potassium hydroxide to obtain the corresponding hydrazinecarbodithioate salts which were then treated in two ways with (i) sulfuric acid and (ii) hydrochloric acid at cooled temperature to furnish the corresponding 1,3,4-thiadiazole and 1,3,4-oxadiazole intermediates, respectively, which were then treated with piperazine bases in the presence of formalin in methanol to furnish the final N-Mannich products 7i-10vi. The newer analogs were examined for their antimicrobial activity against five bacteria (S. aureus and B. cereus, E. coli, P. aeruginosa and K. pneumoniae) and two fungi (A. niger and C. albicans) and the results revealed that compounds demonstrated excellent activity (MICs: 3.12-25 μg/mL) as compared with the standards (MICs: 6.25-25 μg/mL).

  合成并表征了两系列的1,3,4-噻二唑和1,3,4-呋喃二唑衍生物，使用了元素分析和谱学数据（红外光谱、1H-NMR）。将4-羟基喹啉和香豆素部分的肼酰胺衍生物在含有乙醇的氢氧化钾的碳二硫化物中回流，以获得相应的肼甲基二硫酸盐。随后，将其以两种方式处理：(i) 硫酸和 (ii) 盐酸，均在低温下进行，分别得到相应的1,3,4-噻二唑和1,3,4-呋喃二唑中间体。这些中间体再与哌嗪碱基在甲醇中与福尔malin反应，最终合成N-曼尼赫产物7i-10vi。这些新型类似物的抗微生物活性被测试，针对五种细菌（葡萄球菌、蜡样芽孢杆菌、大肠杆菌、铜绿假单胞菌和肺炎克雷伯菌）和两种真菌（黑曲霉和白念珠菌），结果显示这些化合物表现出很好的活性（最低抑菌浓度：3.12-25 μg/mL），相比标准（最低抑菌浓度：6.25-25 μg/mL）。
• New Coumarin Derivatives as Anti-Breast and Anti-Cervical Cancer Agents Targeting VEGFR-2 and p38α MAPK
  作者：Rasha Z. Batran、Dina H. Dawood、Samia A. El-Seginy、Mamdouh M. Ali、Timothy J. Maher、Kuljeet S. Gugnani、Alejandro N. Rondon-Ortiz

  DOI：10.1002/ardp.201700064

  日期：2017.9

  compounds showed potent preferential inhibition effects against human VEGFR‐2 and remarkable anticancer activities in the human breast cancer cell line MCF‐7. Compounds 29, 24, and 2 displayed the highest inhibitory activity against VEGFR‐2 (94% inhibition) and they were the most potent anticancer agents toward MCF‐7 cancer cells with IC50 values of 7.90, 8.28, and 8.30 μg/mL, respectively. Compound 13

  乳腺癌和宫颈癌是影响全球女性的最常见的性别特异性癌症。在这项研究中，我们强调了新系列氟化香豆素衍生物的合成、VEGFR-2 和 p38α MAPK 抑制活性，这些衍生物具有多种生物活性化学部分，这些化学部分连接或融合到香豆素核的 3 和/或 4 位。进一步评估了生物活性抑制剂对人 MCF-7 乳腺癌和 HeLa 宫颈癌细胞系的抗增殖作用。大多数测试的化合物对人 VEGFR-2 显示出有效的优先抑制作用，并在人乳腺癌细胞系 MCF-7 中显示出显着的抗癌活性。化合物 29、24、和 2 对 VEGFR-2 显示出最高的抑制活性（94% 抑制），它们是对 MCF-7 癌细胞最有效的抗癌剂，IC50 值分别为 7.90、8.28 和 8.30 μg/mL。化合物 13 抑制 p38α MAPK 磷酸化，并在 10 和 30 µM 时显着降低细胞对 HeLa 癌细胞的存活率。对 VEGFR-2 和
• 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。
• Antifungal Activities of New Coumarins
  作者：Ahmed A. Al-Amiery、Abdul Amir Hassan Kadhum、Abu Bakar Mohamad

  DOI：10.3390/molecules17055713

  日期：——

  Newly synthesized coumarins 4-((5-mercapto-4-phenyl-4H-1,2,4-triazol-3-yl)-methoxy)-2H-chromen-2-one and 4-((5-(phenylamino)-1,3,4-thiadiazol-2-yl)-methoxy)-2H-chromen-2-one were tested against selected types of fungi and showed significant activities. DFT calculations of the synthesized coumarins were performed using molecular structures with optimized geometries. Molecular orbital calculations provide a detailed description of the orbitals, including spatial characteristics, nodal patterns, and the contributions of individual atoms.

  新合成的香豆素4-((5-巯基-4-苯基-4H-1,2,4-三唑-3-基)-甲氧基)-2H-香豆素-2-酮和4-((5-(苯胺基)-1,3,4-噻二唑-2-基)-甲氧基)-2H-香豆素-2-酮被测试对选定类型的真菌显示出显著的活性。利用优化几何结构的分子结构对合成的香豆素进行了DFT计算。分子轨道计算提供了轨道的详细描述，包括空间特性、节点模式和各个原子的贡献。
• Synthesis, spectroscopy and electrochemistry of new 4-(4-acetyl-5- substituted-4, 5-dihydro-1, 3,4-oxodiazol-2-yl)methoxy)-2H-chromen-2-ones as a novel class of potential antibacterial and antioxidant derivatives
  作者：N. Hamdi、V. Passarelli、A. Romerosa

  DOI：10.1016/j.crci.2010.11.001

  日期：2011.6

  Résumé The synthesis of the new 4-(4-acetyl-5- substituted -4, 5-dihydro-1,3,4-oxodiazol-2-yl)methoxy)-2H-chromen-2-ones derivatives 5 was accomplished by the use of 4-hydroxycoumarine as a starting material. The structures of the compounds were confirmed by analytical UV, IR, 1H, 13C-NMR, NOESY and HMBC NMR spectra to elucidate the different positions of protons and carbons. All the compounds exhibited one quasireversible redox process. The UV absorption spectra of the obtained compounds showed strong absorption bands between 264 and 291 nm assigned to π-π * transitions of the oxadiazole group. All the newly synthesized compounds were screened for their antibacterial and antioxidant activities. Antimicrobial studies revealed that compounds 5a and 5b showed significant antibacterial activity against Escherichia coli and Pseudomonas Aeruginosa 27853. Furthermore these compounds showed antioxidant activities of different extents with respect to individual compounds as well as to the antioxidant methods. The compounds 5a-d was found to be the most active antioxidant in the series then Trolox, which makes the investigated complexes promising a new class of antibacterial compounds.

  简历 通过使用4-羟基香豆素作为起始材料，成功合成了新的4-(4-乙酰基-5-取代-4,5-二氢-1,3,4-噁二唑-2-基)甲氧基)-2H-色烯-2-酮衍生物5。通过分析UV、IR、1H、13C-NMR、NOESY和HMBC NMR光谱确认了这些化合物的结构，以阐明不同位置的质子和碳。所有化合物均显示一个准可逆的氧化还原过程。获得的化合物的UV吸收光谱显示了位于264至291 nm之间的强吸收带，归因于噁二唑基团的π-π*跃迁。所有新合成的化合物均进行了抗菌和抗氧化活性筛选。抗微生物研究表明，化合物5a和5b对大肠杆菌和铜绿假单胞菌27853显示出显著的抗菌活性。此外，这些化合物根据个别化合物和抗氧化方法的不同，显示出不同程度的抗氧化活性。化合物5a-d被发现是该系列中最有效的抗氧化剂，超过了Trolox，这使得所研究的络合物具有作为新一代抗菌化合物的潜力。