(4Z)-3-methyl-4-((phenylamino)(naphthalen-2-yl)methylene)-1-phenyl-1H-pyrazol-5(4H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4Z)-3-methyl-4-((phenylamino)(naphthalen-2-yl)methylene)-1-phenyl-1H-pyrazol-5(4H)-one
• 化学式: C₂₇H₂₁N₃O
• 分子量: 403.483
• InChiKey: BNKBNOFPJZBYPL-QPLCGJKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  44.7
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [RuCl2(benzene)]2 、 (4Z)-3-methyl-4-((phenylamino)(naphthalen-2-yl)methylene)-1-phenyl-1H-pyrazol-5(4H)-one 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 25.0h， 生成 [Ru(η⁶-benzene)((4Z)-3-methyl-4-((phenylamino)(naphthalen-2-yl)methylene)-1-phenyl-1H-pyrazol-5(4H)-one(-H)-κ²N,O)Cl]
  参考文献：
  名称：

  Cytotoxicity of Ruthenium–Arene Complexes Containing β-Ketoamine Ligands

  摘要：

  New ruthenium(II) arene derivatives (arene = p-cymene, benzene, hexamethylbenzene) containing beta-ketoamine ligands L' (HL' in general; in detail, HLph,ph = (4Z)-3-methyl-4-((phenylamino)(phenyl)methylene)-1-phenyl-1H-pyrazol-5(4H)-one, HLnaph,ph = (4Z)-3-methyl-4-((phenyamino)(naphthalen-2-yl)methylene)-1-phenyl-1H-pyrazol-5(4H)- one, HLet,ph = (4Z)-3-methyl-4-(1-(phenylamino)propylidene)-1-phenyl-1Hpyrazol-5(4H)-one) have been synthesized and characterized by spectroscopy (IR, ESI-MS, H-1 and C-13 NMR) and elemental analysis. The ligands in the anionic form coordinate ruthenium in a chelating kappa N-2,O-bidentate fashion, affording 1:1 derivatives of the formula [Ru(arene)(L')Cl]. Further reaction of [Ru(p-cymene)(L')Cl] with AgPF6 or PTA (PTA = 1,3,5-triaza-7-phosphaadamantane) in methanol affords [Ru(p-cymene)(L')(CH3OH)] [PF6] and [Ru(p-cymene) (L')(PTA)]Cl, respectively. The solid-state structures of the ligand HLet,ph and complexes [Ru(p-cymene)(L-ph,L-ph)Cl] (1), [Ru(p-cymene)(L-naph,L-ph)Cl] (4), and [Ru(p-cymene)(L-et,L-ph)Cl] (7) have been determined by single-crystal X-ray diffraction. The antitumor activity of both the ligands and complexes has been evaluated against the human ovarian carcinoma cell line A2780 and its cisplatin-resistant equivalent A2780R, some of the complexes showing significant cytotoxicity toward the cisplatin-resistant cell line.

  DOI：

  10.1021/om301115e
• 作为产物：
  描述：

  3-methyl-1-phenyl-4-(1-naphthoyl)-5-pyrazolone 、 苯胺 以 乙醇 为溶剂， 反应 24.0h， 生成 (4Z)-3-methyl-4-((phenylamino)(naphthalen-2-yl)methylene)-1-phenyl-1H-pyrazol-5(4H)-one
  参考文献：
  名称：

  Cytotoxicity of Ruthenium–Arene Complexes Containing β-Ketoamine Ligands

  摘要：

  New ruthenium(II) arene derivatives (arene = p-cymene, benzene, hexamethylbenzene) containing beta-ketoamine ligands L' (HL' in general; in detail, HLph,ph = (4Z)-3-methyl-4-((phenylamino)(phenyl)methylene)-1-phenyl-1H-pyrazol-5(4H)-one, HLnaph,ph = (4Z)-3-methyl-4-((phenyamino)(naphthalen-2-yl)methylene)-1-phenyl-1H-pyrazol-5(4H)- one, HLet,ph = (4Z)-3-methyl-4-(1-(phenylamino)propylidene)-1-phenyl-1Hpyrazol-5(4H)-one) have been synthesized and characterized by spectroscopy (IR, ESI-MS, H-1 and C-13 NMR) and elemental analysis. The ligands in the anionic form coordinate ruthenium in a chelating kappa N-2,O-bidentate fashion, affording 1:1 derivatives of the formula [Ru(arene)(L')Cl]. Further reaction of [Ru(p-cymene)(L')Cl] with AgPF6 or PTA (PTA = 1,3,5-triaza-7-phosphaadamantane) in methanol affords [Ru(p-cymene)(L')(CH3OH)] [PF6] and [Ru(p-cymene) (L')(PTA)]Cl, respectively. The solid-state structures of the ligand HLet,ph and complexes [Ru(p-cymene)(L-ph,L-ph)Cl] (1), [Ru(p-cymene)(L-naph,L-ph)Cl] (4), and [Ru(p-cymene)(L-et,L-ph)Cl] (7) have been determined by single-crystal X-ray diffraction. The antitumor activity of both the ligands and complexes has been evaluated against the human ovarian carcinoma cell line A2780 and its cisplatin-resistant equivalent A2780R, some of the complexes showing significant cytotoxicity toward the cisplatin-resistant cell line.

  DOI：

  10.1021/om301115e

文献信息

• Cytotoxicity of Ruthenium–Arene Complexes Containing β-Ketoamine Ligands
  作者：Riccardo Pettinari、Claudio Pettinari、Fabio Marchetti、Catherine M. Clavel、Rosario Scopelliti、Paul J. Dyson

  DOI：10.1021/om301115e

  日期：2013.1.14

  New ruthenium(II) arene derivatives (arene = p-cymene, benzene, hexamethylbenzene) containing beta-ketoamine ligands L' (HL' in general; in detail, HLph,ph = (4Z)-3-methyl-4-((phenylamino)(phenyl)methylene)-1-phenyl-1H-pyrazol-5(4H)-one, HLnaph,ph = (4Z)-3-methyl-4-((phenyamino)(naphthalen-2-yl)methylene)-1-phenyl-1H-pyrazol-5(4H)- one, HLet,ph = (4Z)-3-methyl-4-(1-(phenylamino)propylidene)-1-phenyl-1Hpyrazol-5(4H)-one) have been synthesized and characterized by spectroscopy (IR, ESI-MS, H-1 and C-13 NMR) and elemental analysis. The ligands in the anionic form coordinate ruthenium in a chelating kappa N-2,O-bidentate fashion, affording 1:1 derivatives of the formula [Ru(arene)(L')Cl]. Further reaction of [Ru(p-cymene)(L')Cl] with AgPF6 or PTA (PTA = 1,3,5-triaza-7-phosphaadamantane) in methanol affords [Ru(p-cymene)(L')(CH3OH)] [PF6] and [Ru(p-cymene) (L')(PTA)]Cl, respectively. The solid-state structures of the ligand HLet,ph and complexes [Ru(p-cymene)(L-ph,L-ph)Cl] (1), [Ru(p-cymene)(L-naph,L-ph)Cl] (4), and [Ru(p-cymene)(L-et,L-ph)Cl] (7) have been determined by single-crystal X-ray diffraction. The antitumor activity of both the ligands and complexes has been evaluated against the human ovarian carcinoma cell line A2780 and its cisplatin-resistant equivalent A2780R, some of the complexes showing significant cytotoxicity toward the cisplatin-resistant cell line.