3-<α-Imino-benzyl>-4-hydroxy-cumarin | 94064-85-4

• 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: 3-<α-Imino-benzyl>-4-hydroxy-cumarin
• 英文别名: 3-(1-aminobenzylidene)-2H-chromene-2,4(3H)-dione；3-(Amino-phenyl-methylene)chroman-2,4-dione；3-(benzenecarboximidoyl)-4-hydroxychromen-2-one
• CAS: 94064-85-4
• 化学式: C₁₆H₁₁NO₃
• 分子量: 265.268
• InChiKey: QOEWUJOBNRLWJH-UHFFFAOYSA-N

物化性质

• 熔点：
  236.3-237.4 °C(Solv: methanol (67-56-1))
• 沸点：
  473.0±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-<α-Imino-benzyl>-4-hydroxy-cumarin 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 以 二氯甲烷 、 异丙醇 为溶剂， 反应 24.0h， 以43.03%的产率得到[(η⁶-p-cymene)ruthenium(II)chlorido-3-(1-aminobenzylidene)-2H-chromeno-2,4-(3H)-dione-κ²-(N,O)]
  参考文献：
  名称：

  Spectroscopic and cytotoxic characteristics of (p-cymene)Ru(II) complexes with bidentate coumarins and density functional theory comparison with selected Pd(II) complexes

  摘要：

  This paper presents the synthesis of two new (p-cymene)-ruthenium(II) complexes 3a,b with the bidentate coumarin ligands 2a,b. Both complexes were characterized by FTIR spectroscopy, H-1 NMR, C-13 NMR, MS, elemental analysis and DFT calculations. The X-ray structure of complex 3a was also solved. The cytotoxic properties of both complexes were examined on human leukemia NALM-6 and HL-60 cells and melanoma WM-115 cells. The complexes possess higher cytotoxic activity than the ligands, but distinctive result is for complex 3b, which exhibited higher cytotoxic effect on WM-115 cells (IC50 = 60.2 +/- 7.8 mu M) in comparison to carboplatin (IC50 = 422.2 +/- 50.2 mu M). The results of DFT calculations performed at the BP86-D3/QZ4P level for Ru(II) complexes and Pd(II) complexes with the same ligands indicate that Pd(II) complexes are more lipophilic. Moreover the RP-TLC-Based Lipophilicity assessment was also performed. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2016.10.036
• 作为产物：
  描述：

  ethyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate 在 ammonium hydroxide 作用下， 反应 24.0h， 生成 3-<α-Imino-benzyl>-4-hydroxy-cumarin
  参考文献：
  名称：

  Spectroscopic and cytotoxic characteristics of (p-cymene)Ru(II) complexes with bidentate coumarins and density functional theory comparison with selected Pd(II) complexes

  摘要：

  This paper presents the synthesis of two new (p-cymene)-ruthenium(II) complexes 3a,b with the bidentate coumarin ligands 2a,b. Both complexes were characterized by FTIR spectroscopy, H-1 NMR, C-13 NMR, MS, elemental analysis and DFT calculations. The X-ray structure of complex 3a was also solved. The cytotoxic properties of both complexes were examined on human leukemia NALM-6 and HL-60 cells and melanoma WM-115 cells. The complexes possess higher cytotoxic activity than the ligands, but distinctive result is for complex 3b, which exhibited higher cytotoxic effect on WM-115 cells (IC50 = 60.2 +/- 7.8 mu M) in comparison to carboplatin (IC50 = 422.2 +/- 50.2 mu M). The results of DFT calculations performed at the BP86-D3/QZ4P level for Ru(II) complexes and Pd(II) complexes with the same ligands indicate that Pd(II) complexes are more lipophilic. Moreover the RP-TLC-Based Lipophilicity assessment was also performed. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2016.10.036

文献信息

• Synthesis, Cytotoxic Effect, and Structure−Activity Relationship of Pd(II) Complexes with Coumarin Derivatives
  作者：Elżbieta Budzisz、Magdalena Małecka、Ingo-Peter Lorenz、Peter Mayer、Renata A. Kwiecień、Piotr Paneth、Urszula Krajewska、Marek Rózalski

  DOI：10.1021/ic0605569

  日期：2006.11.1

  report the influence of the substituent at the N atom of the ligands on the synthesis, biological activity, and stability of Pd(II) complexes of the general formula PdL(2). The compounds adopt a cis or trans configuration with respect to the substituent at the nitrogen atom. Sterically hindered substituents promote the formation of trans isomers, whereas when the nitrogen atom is unsubstituted, cis isomers

  我们报道了在配体的N原子上的取代基对通式PdL（2）的Pd（II）配合物的合成，生物学活性和稳定性的影响。化合物相对于氮原子上的取代基采用顺式或反式构型。受位阻的取代基促进反式异构体的形成，而当氮原子未被取代时，则形成顺式异构体。通过元素分析，红外和1H NMR光谱以及电喷雾质谱对化合物进行表征。还使用X射线衍射和计算DFT方法研究了配合物。顺式3a和反式3c都在Pd（II）原子周围显示出正方形的几何形状。检查了这些复合物对两种人类白血病细胞系HL-60和NALM-6的细胞毒性作用。钯复合物cis-3a表现出明显的细胞毒活性。这种复合物表现出的作用与卡铂报道的作用相当。Loigand 2a没有细胞毒性。在PB / B3LYP / LACVP ** // mPW1PW91 / LAnL2DZ水平上进行的计算分析显示，顺式和反式异构体的能量差与细胞毒性活性之间具有极好的相关性，从而使计算成为设计新药的有用预测工具。