2-amino-6-chloro-11H-indolo[3,2-c]quinoline | 1418413-99-6

• 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: 2-amino-6-chloro-11H-indolo[3,2-c]quinoline
• 英文别名: 2-amino-6-chloroindolo[3,2-c]quinoline
• CAS: 1418413-99-6
• 化学式: C₁₅H₁₀ClN₃
• 分子量: 267.717
• InChiKey: SOZYNNRWBSWPGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.7
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 2-amino-6-chloro-11H-indolo[3,2-c]quinoline 反应 24.0h， 以83%的产率得到2-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
• 作为产物：
  描述：

  6-chloro-2-nitro-11H-indolo[3,2-c]quinoline 在 铁粉 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以95%的产率得到2-amino-6-chloro-11H-indolo[3,2-c]quinoline
  参考文献：
  名称：

  含吲哚[3,2-c]-喹啉的金属-芳烃配合物：钌与锇的影响以及内酰胺单元的修饰对分子间相互作用、抗癌活性、细胞周期和细胞积累的影响

  摘要：

  六个新颖钌（II） -和锇（II）配合物-arene三吲哚并改性并[3,2- Ç〕喹啉原位由2- aminoindoloquinolines和[M的存在下2-吡啶甲醛开始（已经合成了P-伞花烃)Cl 2 ] 2 (M = Ru, Os) 在乙醇中。所有配合物均已通过元素分析、光谱技术（1 H、13 C NMR、IR、UV-vis）和 ESI 质谱进行表征，同时通过 X 射线衍射研究了四种配合物。已在 A549（非小细胞肺）、SW480（结肠）和 CH1（卵巢）人类癌细胞系中测试了复合物的体外抗增殖活性，并显示 IC 50值介于 1.3 和 >80 μM 之间。报道了 Ru 对 Os 和内酰胺单位修饰对分子间相互作用、抗增殖活性和细胞周期的影响。已经研究了一种钌复合物及其锇类似物的体内抗癌活性，其腹膜内和口服应用对鼠结肠癌模型 CT-26。有趣的是，与钌对应物相比，锇 (II) 复合物显示出

  DOI：

  10.1021/om3012272