2-benzoylpyridine 4,4-dimethyl-3-thiosemicarbazone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-benzoylpyridine 4,4-dimethyl-3-thiosemicarbazone
• 英文别名: 3,3-Dimethyl-1-{[phenyl(pyridin-2-yl)methylidene]amino}thiourea；1,1-dimethyl-3-[(Z)-[phenyl(pyridin-2-yl)methylidene]amino]thiourea
• 化学式: C₁₅H₁₆N₄S
• 分子量: 284.385
• InChiKey: KUHVCGKIRQEOHA-VKAVYKQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯甲酰吡啶 、 4,4-二甲基-3-氨基硫脲单水合物 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 以86%的产率得到2-benzoylpyridine 4,4-dimethyl-3-thiosemicarbazone
  参考文献：
  名称：

  Design, Synthesis, and Characterization of Novel Iron Chelators:  Structure−Activity Relationships of the 2-Benzoylpyridine Thiosemicarbazone Series and Their 3-Nitrobenzoyl Analogues as Potent Antitumor Agents

  摘要：

  Previously, we demonstrated that the potent antiproliferative activity of the di-2-pyridylketone thiosemicarbazone (DpT) series of Fe chelators was due to their ability to induce Fe depletion and form redox-active Fe complexes (Richardson, D. R.; et al. J. Med. Chem. 2006, 49, 6510-6521). We now examine the role of aromatic substituents on the antiproliferative and redox activity of novel DpT analogues, namely, the 2-benzoylpyridine thiosemicarbazone (BpT) and 2-(3-nitrobenzoyl)pyridine thiosemicarbazone (NBpT) series. Both series exhibited selective antiproliferative effects, with the majority having greater antineoplastic activity than their DpT homologues. This makes the BpT chelators the most active anticancer agents developed within our laboratory. The BpT series Fe complexes exhibit lower redox potentials than their corresponding DpT and NBpT complexes, highlighting their enhanced redox activity. The increased ability of BpT-Fe complexes to catalyze ascorbate oxidation and benzoate hydroxylation, relative to their DpT and NBpT analogues, suggested that redox cycling plays an important role in their antiproliferative activity.

  DOI：

  10.1021/jm070445z

文献信息

• Design, Synthesis, and Characterization of Novel Iron Chelators:  Structure−Activity Relationships of the 2-Benzoylpyridine Thiosemicarbazone Series and Their 3-Nitrobenzoyl Analogues as Potent Antitumor Agents
  作者：Danuta S. Kalinowski、Yu、Philip C. Sharpe、Mohammad Islam、Yi-Tyng Liao、David B. Lovejoy、Naresh Kumar、Paul V. Bernhardt、Des R. Richardson

  DOI：10.1021/jm070445z

  日期：2007.7.1

  Previously, we demonstrated that the potent antiproliferative activity of the di-2-pyridylketone thiosemicarbazone (DpT) series of Fe chelators was due to their ability to induce Fe depletion and form redox-active Fe complexes (Richardson, D. R.; et al. J. Med. Chem. 2006, 49, 6510-6521). We now examine the role of aromatic substituents on the antiproliferative and redox activity of novel DpT analogues, namely, the 2-benzoylpyridine thiosemicarbazone (BpT) and 2-(3-nitrobenzoyl)pyridine thiosemicarbazone (NBpT) series. Both series exhibited selective antiproliferative effects, with the majority having greater antineoplastic activity than their DpT homologues. This makes the BpT chelators the most active anticancer agents developed within our laboratory. The BpT series Fe complexes exhibit lower redox potentials than their corresponding DpT and NBpT complexes, highlighting their enhanced redox activity. The increased ability of BpT-Fe complexes to catalyze ascorbate oxidation and benzoate hydroxylation, relative to their DpT and NBpT analogues, suggested that redox cycling plays an important role in their antiproliferative activity.