nitrilotris{1-(2-ethyl)-3-hydroxy-2-methylpyrid-4-one} | 141056-29-3

• 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: nitrilotris{1-(2-ethyl)-3-hydroxy-2-methylpyrid-4-one}
• 英文别名: 2,2',2''-tris[3-hydroxy-2-methyl-4(1H)-pyridinon-1-yl]triethylamine；1-[2-[Bis[2-(3-hydroxy-2-methyl-4-oxopyridin-1-yl)ethyl]amino]ethyl]-3-hydroxy-2-methylpyridin-4-one；1-[2-[bis[2-(3-hydroxy-2-methyl-4-oxopyridin-1-yl)ethyl]amino]ethyl]-3-hydroxy-2-methylpyridin-4-one
• CAS: 141056-29-3
• 化学式: C₂₄H₃₀N₄O₆
• 分子量: 470.525
• InChiKey: CRLXPKFSXJFPKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 nitrilotris{1-(2-ethyl)-3-hydroxy-2-methylpyrid-4-one} 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以55%的产率得到2,2',2''-tris[chlorido[3-(oxo-κO)-2-methyl-4(1H)-pyridinonato-κO4](η6-p-cymene)ruthenium(II)]triethylamine
  参考文献：
  名称：

  Influence of the Arene Ligand, the Number and Type of Metal Centers, and the Leaving Group on the in Vitro Antitumor Activity of Polynuclear Organometallic Compounds

  摘要：

  Dinuclear ruthenium complexes were shown to exhibit strong antiproliferative properties in human tumor cell lines. In order to extend the structure-activity relationships (SARs), a series of new Ru-II(arene)X complexes (X = Cl, Br, I) linked by pyridinone-based spacers were synthesized and assayed for their in vitro antineoplastic effect. The SARs were established in terms of the arene ligand. the leaving group (the halide ligand), and the nature and number of the metal centers. It was demonstrated that, besides the previously shown effect or the spacer length, the nature of the metal center has the biggest influence on the in vitro anticancer activity. The halide ligand had no effect on the cytotoxicity, due to rapid formation of the same aquation product for all evaluated compounds. Furthermore, nearly identical activity was observed when varying the arene ligand from p-cymene to biphenyl. However, the number of metal centers was found to be important, with the dinuclear compound being more active than the analogous mono- and trinuclear species.

  DOI：

  10.1021/om900715j

文献信息

• Comparative iron binding studies of bis- and tris(3-hydroxy-2-methylpyrid-4-ones) and desferrioxamine
  作者：L.N. Sheppard、G.J. Kontoghiorghes

  DOI：10.1016/s0020-1693(00)80369-2

  日期：1991.10

  The iron binding properties of three tetradentate and one hexadentate 3-hydroxy-2-methylpyrid-4-one chelators, intended for clinical use, were studied using visible spectrophotometry and compared to the iron binding of desferrioxamine at both acidic and neutral pH using Job plot estimations. The chelators bis(3-hydroxy-2-methylpyrid-4-one) (bis(L1)), nitrilotris[1-(2-ethyl)-3-hydroxy-2-methylpyrid-4-one] (tris(ethyl L1)), 1,4-bis(3-hydroxy-2-methylpyrid-4-one)butane (bis(ethyl L1)) and 1,6-bis(3-hydroxy-2-methylpyrid-4-one)hexane (bis(propyl L1)) appear to form a mixture of iron complexes at pH 2 of more than one of the following chelator:iron stoichiometries: 1:1, 1:2 and 2:3. In contrast, at pH 7.4, bis(L1) and tris(ethyl L1) appear to form a complex with a higher chelator:iron molar ratio of 3:2. Desferrioxamine differed from the oligomeric 3-hydroxy-2-methylpyrid-4-ones by forming a 1:1 chelator:iron complex both at pH 2 and 7.4. The differences in the stoichiometry of iron complexes between desferrioxamine and oligomeric 3-hydroxy-2-methylpyrid-4-one may have implications in the mode of action of these chelators in vivo. In particular the higher iron binding capacity of oligomeric 3-hydroxy-2-methylpyrid-4-ones at acidic pH may have application in the treatment of acute iron poisoning and other conditions of iron overload caused by increased gastrointestinal absorption.
• Influence of the Arene Ligand, the Number and Type of Metal Centers, and the Leaving Group on the <i>in Vitro</i> Antitumor Activity of Polynuclear Organometallic Compounds
  作者：Maria G. Mendoza-Ferri、Christian G. Hartinger、Alexey A. Nazarov、Rene E. Eichinger、Michael A. Jakupec、Kay Severin、Bernhard K. Keppler

  DOI：10.1021/om900715j

  日期：2009.11.9

  Dinuclear ruthenium complexes were shown to exhibit strong antiproliferative properties in human tumor cell lines. In order to extend the structure-activity relationships (SARs), a series of new Ru-II(arene)X complexes (X = Cl, Br, I) linked by pyridinone-based spacers were synthesized and assayed for their in vitro antineoplastic effect. The SARs were established in terms of the arene ligand. the leaving group (the halide ligand), and the nature and number of the metal centers. It was demonstrated that, besides the previously shown effect or the spacer length, the nature of the metal center has the biggest influence on the in vitro anticancer activity. The halide ligand had no effect on the cytotoxicity, due to rapid formation of the same aquation product for all evaluated compounds. Furthermore, nearly identical activity was observed when varying the arene ligand from p-cymene to biphenyl. However, the number of metal centers was found to be important, with the dinuclear compound being more active than the analogous mono- and trinuclear species.