8-amino-6-(4-methylpiperazin-1-yl)indolo[3,2-c]quinoline | 1613468-97-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-amino-6-(4-methylpiperazin-1-yl)indolo[3,2-c]quinoline
• CAS: 1613468-97-5
• 化学式: C₂₀H₂₁N₅
• 分子量: 331.42
• InChiKey: ZXHLEGQTDQGQEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.18
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  吡啶-2-甲醛 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 8-amino-6-(4-methylpiperazin-1-yl)indolo[3,2-c]quinoline 、 水 以 乙醇 为溶剂， 反应 20.0h， 以60%的产率得到(η⁶-p-cymene)[6-(4-methylpiperazin-1-yl)-κN-(pyridin-2-ylmethylene)-11H-indolo[3,2-c]quinolin-8-κN-amine]chloridoruthenium(II) chloride - water (1/2.5H2O)
  参考文献：
  名称：

  Effect of the Piperazine Unit and Metal-Binding Site Position on the Solubility and Anti-Proliferative Activity of Ruthenium(II)- and Osmium(II)- Arene Complexes of Isomeric Indolo[3,2-c]quinoline—Piperazine Hybrids

  摘要：

  In this study, the indoloquinoline backbone and piperazine were combined to prepare indoloquinoline-piperazine hybrids and their ruthenium- and osmium-arene complexes in an effort to generate novel antitumor agents with improved aqueous solubility. In addition, the position of the metal-binding unit was varied, and the effect of these structural alterations on the aqueous solubility and antiproliferative prepared in situ and isolated as six ruthenium and osmium activity of their ruthenium- and osmium-arene complexes was studied. The indoloquinoline-piperazine hybrids L1-3 were complexes [(eta(6)-p-cymene)M(L1-3)Cl]Cl, where L-1 = 6-(4-methylpiperazin-1-yl)-N-(pyridin-2-yl-methylene)-11H-indolo-[3,2-c]quinolin-2-N-amine, M = Ru ([1a]Cl), Os ([1b]Cl), L-2 = 6-(4-methylpiperazin-1-yl)-N-(pyriclin-2-yl-methylene)-11H-indolo[3,2-c]quinolin-4-N-amine, M = Ru ([2a]Cl), Os ([2b]Cl), L-3 = 6-(4-methylpiperazin-l-yl)-N-(pyridin-2-yl-methylene)11H-indolo[3,2-c]quinolin-8-N-amine, M = Ru ([3a]Cl), Os ([313]Cl). The compounds were characterized by elemental analysis, one- and two-dimensional NMR spectroscopy, ESI mass spectrometry, IR and UV-vis spectroscopy, and single-crystal X-ray diffraction. The antiproliferative activity of the isomeric ruthenium and osmium complexes [1a,b]Cl-[3a,b]Cl was examined in vitro and showed the importance of the position of the metal-binding site for their cytotoxicity. Those complexes containing the metal-binding site located at the position 4 of the indoloquinoline scaffold ([2a]Cl and [2b]Cl) demonstrated the most potent antiproliferative activity. The results provide important insight into the structure-activity relationships of ruthenium- and osmium-arene complexes with indoloquinoline-piperazine hybrid ligands. These studies can be further utilized for the design and development of more potent chemotherapeutic agents.

  DOI：

  10.1021/ic500825j
• 作为产物：
  描述：

  6-chloro-8-nitroindolo[3,2-c]quinoline 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 8-amino-6-(4-methylpiperazin-1-yl)indolo[3,2-c]quinoline
  参考文献：
  名称：

  Effect of the Piperazine Unit and Metal-Binding Site Position on the Solubility and Anti-Proliferative Activity of Ruthenium(II)- and Osmium(II)- Arene Complexes of Isomeric Indolo[3,2-c]quinoline—Piperazine Hybrids

  摘要：

  In this study, the indoloquinoline backbone and piperazine were combined to prepare indoloquinoline-piperazine hybrids and their ruthenium- and osmium-arene complexes in an effort to generate novel antitumor agents with improved aqueous solubility. In addition, the position of the metal-binding unit was varied, and the effect of these structural alterations on the aqueous solubility and antiproliferative prepared in situ and isolated as six ruthenium and osmium activity of their ruthenium- and osmium-arene complexes was studied. The indoloquinoline-piperazine hybrids L1-3 were complexes [(eta(6)-p-cymene)M(L1-3)Cl]Cl, where L-1 = 6-(4-methylpiperazin-1-yl)-N-(pyridin-2-yl-methylene)-11H-indolo-[3,2-c]quinolin-2-N-amine, M = Ru ([1a]Cl), Os ([1b]Cl), L-2 = 6-(4-methylpiperazin-1-yl)-N-(pyriclin-2-yl-methylene)-11H-indolo[3,2-c]quinolin-4-N-amine, M = Ru ([2a]Cl), Os ([2b]Cl), L-3 = 6-(4-methylpiperazin-l-yl)-N-(pyridin-2-yl-methylene)11H-indolo[3,2-c]quinolin-8-N-amine, M = Ru ([3a]Cl), Os ([313]Cl). The compounds were characterized by elemental analysis, one- and two-dimensional NMR spectroscopy, ESI mass spectrometry, IR and UV-vis spectroscopy, and single-crystal X-ray diffraction. The antiproliferative activity of the isomeric ruthenium and osmium complexes [1a,b]Cl-[3a,b]Cl was examined in vitro and showed the importance of the position of the metal-binding site for their cytotoxicity. Those complexes containing the metal-binding site located at the position 4 of the indoloquinoline scaffold ([2a]Cl and [2b]Cl) demonstrated the most potent antiproliferative activity. The results provide important insight into the structure-activity relationships of ruthenium- and osmium-arene complexes with indoloquinoline-piperazine hybrid ligands. These studies can be further utilized for the design and development of more potent chemotherapeutic agents.

  DOI：

  10.1021/ic500825j