3-(ferrocenylamido)-5-methylpyrazole | 850134-92-8

• 英文名称: 3-(ferrocenylamido)-5-methylpyrazole
• 英文别名: 3-ferrocenylamido-5-methylpyrazole；3-Fc-AMP
• CAS: 850134-92-8
• 化学式: C₁₅H₁₅FeN₃O
• 分子量: 309.151
• InChiKey: ITTSQDMXNVTXTD-UHFFFAOYSA-N

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：

  cadmium(II) perchlorate hexahydrate 、 3-(ferrocenylamido)-5-methylpyrazole 以 甲醇 为溶剂， 以89%的产率得到[Cd(3-ferrocenylamido-5-methylpyrazole)2(methanol)2](ClO4)2
  参考文献：
  名称：

  3-Ferrocenylamido-5-methylpyrazole: synthesis and metal coordination

  摘要：

  The new pyrazole-derived ferrocene ligand 3-ferroceneamido-5-methylpyrazole (3-Fc-AMP, 2) was synthesized from 3-amino-5-methylpyrazole and ferrocenecarboxylic acid. The ligand associates in the solid state into one-dimensional H-bonded polymeric chains and forms N,O-chelating metal complexes of Zn, Cd, Ni and Co, having ML2 and ML3 stoichiometries. Their electrochemical properties and the X-ray crystal structures of two Cd and Ni complexes are reported. (c) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2004.11.008
• 作为产物：
  描述：

  二茂铁甲酸 、 三氟乙酸 、 2-甲基-2-丙基3-氨基-5-甲基-1H-吡唑-1-羧酸酯 在 1-hydroxybenzotriazole 、 dicyclohexyl carbodiimide 、 Et₃N 作用下， 以 乙腈 为溶剂， 以35%的产率得到3-(ferrocenylamido)-5-methylpyrazole
  参考文献：
  名称：

  3-Ferrocenylamido-5-methylpyrazole: synthesis and metal coordination

  摘要：

  The new pyrazole-derived ferrocene ligand 3-ferroceneamido-5-methylpyrazole (3-Fc-AMP, 2) was synthesized from 3-amino-5-methylpyrazole and ferrocenecarboxylic acid. The ligand associates in the solid state into one-dimensional H-bonded polymeric chains and forms N,O-chelating metal complexes of Zn, Cd, Ni and Co, having ML2 and ML3 stoichiometries. Their electrochemical properties and the X-ray crystal structures of two Cd and Ni complexes are reported. (c) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2004.11.008

文献信息

• Synthesis of redox-active ferrocene pyrazole conjugates and their cytotoxicity in human mammary adenocarcinoma MCF-7 cells
  作者：Wilhelmina C.M. Duivenvoorden、You-nian Liu、Gabriele Schatte、Heinz-Bernhard Kraatz

  DOI：10.1016/j.ica.2005.04.010

  日期：2005.7

  The redox-active ferrocenoyl modified pyrazole ligand (3-Fc-AMP) readily coordinates to a variety of transition metal ions. Here, we describe our findings regarding the synthesis and structural characterization of iron and cobalt complexes of Fc-AMP, and the cytotoxicity profiles of these chemicals in vitro. Using the human mammary adenocarcinoma MCF-7 cell line we show that the free ligand and three metal complexes induced cytotoxicity with calculated LC(50)s ranging from 45.8 to 73.2 mu M. The toxicity of the complexes decreased as the redox potential increased. The present study demonstrates the potential chemotherapeutic promise of metal complexes of a redox-active ferrocenoyl modified pyrazole ligand on human cancer cells. (c) 2005 Elsevier B.V. All rights reserved.