2-((4-oxo-4H-chromen-3-yl)methyleneamino)benzoic acid | 1160049-81-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-((4-oxo-4H-chromen-3-yl)methyleneamino)benzoic acid
• 英文别名: 2-{[(4-oxo-4H-chromen-3-yl)methylidene]amino}benzoic acid；(E)-2-((4-oxo-4H-chromen-3-yl)methyleneamino)benzoic acid；2-[(4-oxochromen-3-yl)methylideneamino]benzoic acid
• CAS: 1160049-81-9
• 化学式: C₁₇H₁₁NO₄
• 分子量: 293.279
• InChiKey: JHNVXSSFYWVUAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((4-oxo-4H-chromen-3-yl)methyleneamino)benzoic acid 、 copper(II) acetate monohydrate 以 甲醇 为溶剂， 以80%的产率得到
  参考文献：
  名称：

  Synthesis, structural characterization, fluorescence, antimicrobial, antioxidant and DNA cleavage studies of Cu(II) complexes of formyl chromone Schiff bases

  摘要：

  Cu(II) complexes have been synthesized from different Schiff bases, such as 3-((2-hydroxy phenylimino)methyl)-4H-chromen-4-one (HL1), 2((4-oxo-4H-chromen-3-yl)methylneamino) benzoicacid (HL2), 3((3-hydroxypyridin-2-ylimino)methyl)-4H-chromen-4-one (HL3) and 3((2-mercaptophenylimino)methyl)-4H-chromen-4-one (HL4). The complexes were characterized by analytical, molar conductance, IR, electronic, magnetic, ESR, thermal, powder XRD and SEM studies. The analytical data reveal that metal to ligand molar ratio is 1:2 in all the complexes. Molar conductivity data indicates that all the Cu(II) complexes are neutral. On the basis of magnetic and electronic spectral data, distorted octahedral geometry is proposed for all the Cu(II) complexes. Thermal behaviour of the synthesized complexes illustrates the presence of lattice water molecules in the complexes. X-ray diffraction studies reveal that all the ligands and their Cu(II) complexes have triclinic system with different unit cell parameters. Antimicrobial, antioxidant and DNA cleavage activities indicate that metal complexes exhibited greater activity as compared with ligands. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.10.037
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 三氯氧磷 作用下， 以 甲醇 为溶剂， 生成 2-((4-oxo-4H-chromen-3-yl)methyleneamino)benzoic acid
  参考文献：
  名称：

  Synthesis, structural characterization, fluorescence, antimicrobial, antioxidant and DNA cleavage studies of Cu(II) complexes of formyl chromone Schiff bases

  摘要：

  Cu(II) complexes have been synthesized from different Schiff bases, such as 3-((2-hydroxy phenylimino)methyl)-4H-chromen-4-one (HL1), 2((4-oxo-4H-chromen-3-yl)methylneamino) benzoicacid (HL2), 3((3-hydroxypyridin-2-ylimino)methyl)-4H-chromen-4-one (HL3) and 3((2-mercaptophenylimino)methyl)-4H-chromen-4-one (HL4). The complexes were characterized by analytical, molar conductance, IR, electronic, magnetic, ESR, thermal, powder XRD and SEM studies. The analytical data reveal that metal to ligand molar ratio is 1:2 in all the complexes. Molar conductivity data indicates that all the Cu(II) complexes are neutral. On the basis of magnetic and electronic spectral data, distorted octahedral geometry is proposed for all the Cu(II) complexes. Thermal behaviour of the synthesized complexes illustrates the presence of lattice water molecules in the complexes. X-ray diffraction studies reveal that all the ligands and their Cu(II) complexes have triclinic system with different unit cell parameters. Antimicrobial, antioxidant and DNA cleavage activities indicate that metal complexes exhibited greater activity as compared with ligands. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.10.037

文献信息

• 3-Formylchromones: Potential antiinflammatory agents
  作者：Khalid M. Khan、Nida Ambreen、Uzma Rasool Mughal、Saima Jalil、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.1016/j.ejmech.2010.05.065

  日期：2010.9

  3-formylchromone (1) and its derivatives 2–24 and evaluation of their potential antiinflammatory activities is reported here. These compounds were characterized by 1H NMR, EI MS, IR, and UV spectroscopic techniques and elemental analysis. The synthesized compounds were evaluated by using various in vitro and in vivo assay models for antiinflammatory activity and their effects were compared with known standard

  -3-甲酰（的合成和表征1）及其衍生物2 - 24其潜在的抗炎活性的和评价此处报告。这些化合物通过1 H NMR，EI MS，IR和UV光谱技术和元素分析进行​​表征。通过使用各种体外和体内测定模型评估合成的化合物的抗炎活性，并将其作用与已知的标准药物（如阿司匹林和消炎痛）进行比较。在所有测试的化合物，1，2，5，6，9，14，16 - 19，21 - 23，显示出有前途的抗炎活性。 结果和比吸收率已在本报告中进行了讨论。
• Schiff bases of 3-formylchromone as thymidine phosphorylase inhibitors
  作者：Khalid Mohammed Khan、Nida Ambreen、Sajjad Hussain、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.1016/j.bmc.2009.03.020

  日期：2009.4

  3-Formylchromone (1), 3-methyl-7-hydroxychromone (2) and Schiff bases of 3-formylchromone 3-19 have been synthesized and their anti-thymidine phosphorylase inhibitory activity was evaluated. Compounds 1-19 showed a varying degree of thymidine phosphorylase inhibition with IC50 values 19.77 +/- 3.25 to 480.21 +/- 2.34 mu M. Their activity was compared with the standard 7-deazaxanthine (IC50 = 39.28 +/- 0.76 mu M). Compound 12 showed an excellent thymidine phosphorylase inhibitory activity with an IC50 value of 19.77 +/- 3.25 mu M, better than the standard. Compound 4 also showed an excellent inhibitory activity (IC50 = 40.29 +/- 4.56 mu M). The parent 3-formylchromone (1) and 3-methyl-7-hydroxychromone (2) were found to be inactive. The structures of the compounds were elucidated by using spectroscopic techniques, including H-1 NMR, EI MS, IR, UV and elemental analysis. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis, structural characterization, fluorescence, antimicrobial, antioxidant and DNA cleavage studies of Cu(II) complexes of formyl chromone Schiff bases
  作者：P. Kavitha、M. Saritha、K. Laxma Reddy

  DOI：10.1016/j.saa.2012.10.037

  日期：2013.2

  Cu(II) complexes have been synthesized from different Schiff bases, such as 3-((2-hydroxy phenylimino)methyl)-4H-chromen-4-one (HL1), 2((4-oxo-4H-chromen-3-yl)methylneamino) benzoicacid (HL2), 3((3-hydroxypyridin-2-ylimino)methyl)-4H-chromen-4-one (HL3) and 3((2-mercaptophenylimino)methyl)-4H-chromen-4-one (HL4). The complexes were characterized by analytical, molar conductance, IR, electronic, magnetic, ESR, thermal, powder XRD and SEM studies. The analytical data reveal that metal to ligand molar ratio is 1:2 in all the complexes. Molar conductivity data indicates that all the Cu(II) complexes are neutral. On the basis of magnetic and electronic spectral data, distorted octahedral geometry is proposed for all the Cu(II) complexes. Thermal behaviour of the synthesized complexes illustrates the presence of lattice water molecules in the complexes. X-ray diffraction studies reveal that all the ligands and their Cu(II) complexes have triclinic system with different unit cell parameters. Antimicrobial, antioxidant and DNA cleavage activities indicate that metal complexes exhibited greater activity as compared with ligands. (C) 2012 Elsevier B.V. All rights reserved.