[Pd{C₆H₄CPh=NH}(μ-Cl)]₂ | 1419590-05-8

• 英文名称: [Pd{C₆H₄CPh=NH}(μ-Cl)]₂
• CAS: 1419590-05-8
• 化学式: C₂₆H₂₀Cl₂N₂Pd₂
• 分子量: 644.204
• InChiKey: GBYUJTKOYOVDRZ-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  [Pd{C₆H₄CPh=NH}(μ-Cl)]₂ 、 三苯基膦 以 丙酮 为溶剂， 反应 2.0h， 以79%的产率得到
  参考文献：
  名称：

  Cyclopalladated benzophenone imines: Synthesis, cytotoxicity against human breast adenocarcinoma cell lines and DNA interaction

  摘要：

  Treatment of benzophenone imine with the stoichiometric amount of Pd(OAc)(2) in acetic acid at 60 degrees C produced the corresponding acetato-bridged five-membered ortho-cyclopalladated dimer [Pd{C6H4CPh = NH}(mu-OAc)](2) (1), which was isolated in pure form in a 79% yield. Reaction of 1 with an excess of LiCl in acetone gave rise to the corresponding chlorido-bridged cyclopalladated dimer [Pd{C6H4CPh = NH}(mu-Cl)](2) (2) in a 78% yield. Compounds 1-2 reacted with an excess of py-d(5) or the stoichiometric amount of PPh3 to give the mononuclear compounds trans-N,L-[Pd{C6H4CPh = NH}(X)(L)] [3 (X = OAc, L = py-d(5)); 4 (X = Cl, L = py-d(5)); 5 (X = OAc, L = PPh3) and 6 (X = Cl, L = PPh3)]. Compounds 2-3 were prepared in CDCl3/py-d(5) solution and were studied by H-1 NMR, but were not isolated. In contrast, compounds 5-6 were prepared in acetone and were isolated in pure form in 43 and 79% yields, respectively. Compounds 1, 2, 5 and 6 were characterized by elemental analyses, mass spectrometry, IR, NMR and electronic spectroscopy. Compounds 1, 2, 5 and 6 showed high antiproliferative activity against MDA-MB231 and MCF7 human breast cancer cell lines, especially, compounds 5-6. These two latter compounds presented greater antiproliferative activity than cisplatin and produced IC50 values in the range 1-5 mu M. The interaction of compounds 1, 2, 5 and 6 with DNA was also studied by the DNA electrophoretic migration, DNA-ethidium bromide fluorescence quenching and viscometry techniques. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.11.034
• 作为产物：
  描述：

  [Pd{C₆H₄CPh=NH}(μ-OAc)]₂ 、 lithium chloride 以 丙酮 为溶剂， 反应 2.0h， 以78%的产率得到[Pd{C₆H₄CPh=NH}(μ-Cl)]₂
  参考文献：
  名称：

  Cyclopalladated benzophenone imines: Synthesis, cytotoxicity against human breast adenocarcinoma cell lines and DNA interaction

  摘要：

  Treatment of benzophenone imine with the stoichiometric amount of Pd(OAc)(2) in acetic acid at 60 degrees C produced the corresponding acetato-bridged five-membered ortho-cyclopalladated dimer [Pd{C6H4CPh = NH}(mu-OAc)](2) (1), which was isolated in pure form in a 79% yield. Reaction of 1 with an excess of LiCl in acetone gave rise to the corresponding chlorido-bridged cyclopalladated dimer [Pd{C6H4CPh = NH}(mu-Cl)](2) (2) in a 78% yield. Compounds 1-2 reacted with an excess of py-d(5) or the stoichiometric amount of PPh3 to give the mononuclear compounds trans-N,L-[Pd{C6H4CPh = NH}(X)(L)] [3 (X = OAc, L = py-d(5)); 4 (X = Cl, L = py-d(5)); 5 (X = OAc, L = PPh3) and 6 (X = Cl, L = PPh3)]. Compounds 2-3 were prepared in CDCl3/py-d(5) solution and were studied by H-1 NMR, but were not isolated. In contrast, compounds 5-6 were prepared in acetone and were isolated in pure form in 43 and 79% yields, respectively. Compounds 1, 2, 5 and 6 were characterized by elemental analyses, mass spectrometry, IR, NMR and electronic spectroscopy. Compounds 1, 2, 5 and 6 showed high antiproliferative activity against MDA-MB231 and MCF7 human breast cancer cell lines, especially, compounds 5-6. These two latter compounds presented greater antiproliferative activity than cisplatin and produced IC50 values in the range 1-5 mu M. The interaction of compounds 1, 2, 5 and 6 with DNA was also studied by the DNA electrophoretic migration, DNA-ethidium bromide fluorescence quenching and viscometry techniques. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.11.034

文献信息

• Cyclopalladated and cycloplatinated benzophenone imines: Antitumor, antibacterial and antioxidant activities, DNA interaction and cathepsin B inhibition
  作者：Joan Albert、Lucía D'Andrea、Jaume Granell、Pepita Pla-Vilanova、Josefina Quirante、Muhammad Kaleem Khosa、Carme Calvis、Ramon Messeguer、Josefa Badía、Laura Baldomà、Mercè Font-Bardia、Teresa Calvet

  DOI：10.1016/j.jinorgbio.2014.07.001

  日期：2014.11

  The antitumor, antibacterial and antioxidant activity, DNA interaction and cathepsin B inhibition of cyclo-ortho-palladated and -platinated compounds [Pd(C,N)](2)(mu-X)(2) [X = OAc (1), X = Cl (2)] and trans-N,P-[M(C,N)X(PPh3)] [M = Pd, X = OAc (3), M = Pd, X = Cl (4), M = Pt, X = Cl (5)] are discussed [(C,N) = cyclo-ortho-metallated benzophenone imine]. The cytotoxicity of compound 5 has been evaluated towards human breast (MDA-MB-231 and MCF-7) and colon (HCT-116) cancer cell lines and that of compounds 1-4 towards the HCT-116 human colon cancer cell line. These cytotoxicities have been compared with those previously reported for compounds 1-4 towards MDA-MB-231 and MCF-7 cancer cell lines. Compound 3 and 4 were approximately four times more active than cisplatin against the MDA-MB-231 and MCF-7 cancer cell lines, and compound 5, was approximately four times more potent than cisplatin against the HCT-116 cancer cell line. The antibacterial activity of compounds 1-5 was in between the ranges of activity of the commercial antibiotic compounds cefixime and roxithromycin. Complexes 1-2 and 4-5 presented also antioxidant activity. Compounds 1-5 alter the DNA tertiary structure in a similar way to cisplatin, but at higher concentration, and do not present a high efficiency as cathepsin B inhibitors. Compound 5 has not been previously described, and its preparation, characterization, and X-ray crystal structure are reported. (C) 2014 Elsevier Inc. All rights reserved.