3-Hydroxy-4-((4-methylpiperazin-1-yl)methyl)pyridin-2(1H)-one | 835614-44-3

• 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: 3-Hydroxy-4-((4-methylpiperazin-1-yl)methyl)pyridin-2(1H)-one
• 英文别名: 3-hydroxy-4-[(4-methylpiperazin-1-yl)methyl]-1H-pyridin-2-one
• CAS: 835614-44-3
• 化学式: C₁₁H₁₇N₃O₂
• 分子量: 223.275
• InChiKey: LAZKSLYLWUJZKO-UHFFFAOYSA-N

物化性质

• 沸点：
  437.6±45.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  55.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [RuCl2(benzene)]2 、 3-Hydroxy-4-((4-methylpiperazin-1-yl)methyl)pyridin-2(1H)-one 、 lithium chloride 在 CsOH 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  pH-Triggered Assembly of Organometallic Receptors for Lithium Ions

  摘要：

  The reaction of half-sandwich complexes of ruthenium, rhodium, and iridium with amino-substituted 3-hydroxy-2-pyridone ligands in aqueous solution gives monomeric O,O'-chelate complexes. Upon addition of base, the complexes assemble to form trimeric metallamacrocycles, as evidenced by NMR spectroscopy and single-crystal X-ray analyses. The macrocycles are able to act as highly selective receptors for lithium ions. The binding constants depend on the nature of the half-sandwich complex. the ligand, and the pH. With a commercially available (cymene)Ru complex, a receptor with a Li-divided by binding Constant of K-a = 5.8 (+/-1.0) x 10(4) M-1 and a Li-divided by-Na+ selectivity of 10 000:1 can be obtained. The fact that the assembly process of the receptor is pH-dependent can be used to detect the presence of lithium ions by a pH measurement. Furthermore, it is possible to transduce the binding of Li-divided by into a change of color by means of a chemical reaction with FeCl3. This allows the detection of Li-divided by in the pharmacologically relevant concentration range of 0.5-1.5 mM by the "naked eye".

  DOI：

  10.1021/ja044874n

文献信息

• Organometallic complexes that interconvert between trimeric and monomeric structures as a function of pH and their effect on human cancer and fibroblast cells
  作者：Wee Han Ang、Zacharias Grote、Rosario Scopelliti、Lucienne Juillerat-Jeanneret、Kay Severin、Paul J. Dyson

  DOI：10.1016/j.jorganchem.2008.11.026

  日期：2009.3

  Organometallic half-sandwich complexes based on ruthenium with aminomethyl-substituted 3-hydroxy-2-pyridone ligands exist in aqueous solution as monomeric O,O'-chelate complexes or trimeric metallamacrocycles depending upon the pH. We hypothesized that administration of the compounds as stable trimers, which subsequently convert to active monomers at the reduced pH of the cancer environment, could facilitate their delivery to cancer cells without undergoing deactivation. Thus, the compounds were evaluated against cancer and fibroblast cell lines in vitro. A series of rhodium complexes, which exist mainly as monomers at neutral pH, were also studied for comparative purposes. (c) 2008 Elsevier B.V. All rights reserved.
• pH-Triggered Assembly of Organometallic Receptors for Lithium Ions
  作者：Zacharias Grote、Rosario Scopelliti、Kay Severin

  DOI：10.1021/ja044874n

  日期：2004.12.1

  The reaction of half-sandwich complexes of ruthenium, rhodium, and iridium with amino-substituted 3-hydroxy-2-pyridone ligands in aqueous solution gives monomeric O,O'-chelate complexes. Upon addition of base, the complexes assemble to form trimeric metallamacrocycles, as evidenced by NMR spectroscopy and single-crystal X-ray analyses. The macrocycles are able to act as highly selective receptors for lithium ions. The binding constants depend on the nature of the half-sandwich complex. the ligand, and the pH. With a commercially available (cymene)Ru complex, a receptor with a Li-divided by binding Constant of K-a = 5.8 (+/-1.0) x 10(4) M-1 and a Li-divided by-Na+ selectivity of 10 000:1 can be obtained. The fact that the assembly process of the receptor is pH-dependent can be used to detect the presence of lithium ions by a pH measurement. Furthermore, it is possible to transduce the binding of Li-divided by into a change of color by means of a chemical reaction with FeCl3. This allows the detection of Li-divided by in the pharmacologically relevant concentration range of 0.5-1.5 mM by the "naked eye".