6-chloro-2-nitro-11H-indolo[3,2-c]quinoline | 1262329-10-1

• 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: 6-chloro-2-nitro-11H-indolo[3,2-c]quinoline
• CAS: 1262329-10-1
• 化学式: C₁₅H₈ClN₃O₂
• 分子量: 297.7
• InChiKey: AKNJWPQLDZCVBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.82
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  在 三氯氧磷 作用下， 反应 24.0h， 生成 6-chloro-2-nitro-11H-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

文献信息

• Synthesis, β-haematin inhibition, and in vitro antimalarial testing of isocryptolepine analogues: SAR study of indolo[3,2-c]quinolines with various substituents at C2, C6, and N11
  作者：Ning Wang、Kathryn J. Wicht、Kento Imai、Ming-qi Wang、Tran Anh Ngoc、Ryo Kiguchi、Marcel Kaiser、Timothy J. Egan、Tsutomu Inokuchi

  DOI：10.1016/j.bmc.2014.03.030

  日期：2014.5

  A series of indolo[3,2-c]quinolines were synthesized by modifying the side chains of the omega-aminoalkylamines at the C6 position and introducing substituents at the C2 position, such as F, Cl, Br, Me, MeO and NO2, and a methyl group at the N11 position for an SAR study. The in vitro antiplasmodial activities of the derivative agents against two different strains (CQS: NF54 and CQR: K1) and the cytotoxic activity against normal L6 cells were evaluated. The test results showed that compounds 6k and 6l containing the branched methyl groups of 3-aminopropylamino at C6 with a Cl atom at C2 exhibited a very low cytotoxicity with IC50 values above 4000 nM, high antimalarial activities with IC50 values of about 11 nM for CQS (NF54), IC50 values of about 17 nM for CQR (K1), and RI resistance indices of 1.6. Furthermore, the compounds were tested for beta-haematic inhibition, and QSAR revealed an interesting linear correlation between the biological activity of CQS (NF54) and three contributing factors, namely solubility, hydrophilic surface area, and beta-haematin inhibition for this series. In vivo testing of 6l showed a reduction in parasitaemia on day 4 with an activity of 38%. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and in vitro cytotoxic effect of 6-amino-substituted 11H- and 11Me-indolo[3,2-c]quinolines
  作者：Ning Wang、Marta Świtalska、Ming-Yu Wu、Kento Imai、Tran Anh Ngoc、Cui-Qing Pang、Li Wang、Joanna Wietrzyk、Tsutomu Inokuchi

  DOI：10.1016/j.ejmech.2014.03.038

  日期：2014.5

  A series of 6-amino-11H- indolo[3,2-c]quinoline derivatives with various substituents on the quinoline ring were synthesized. A methyl group introduced to N-11 of the intermediate 4 to elaborate novel analog 7. The cytotoxic effect of these 6-amino-substituted 11H- and 11-methyl-indolo[3,2-c]quinoline derivatives in vitro were tested against MV4-11 (human leukemia), A549 (non-small cell lung cancer) and HCT116 (colon cancer) and BALB/3T3 (normal murine fibroblasts). All the N-11 methylated compounds significantly increased the cytotoxicity. Compound 7p was most active with the IC50 value of 0.052 mu M against the MV4-11 cell line, and also exhibited a selective activity against A549, HCT116 and BALB/3T3 cell line, with the respective IC50 values of 0.112, 0.007 and 0.083 mu M, which were higher or comparable to those of the anticancer drug doxorubicin HCl. The binding constants of 5g and 7h to salmon fish sperm DNA were also evaluated using UV-vis absorption spectroscopy, indicating intercalation binding with constants of 1.05 x 10(6) L/mol and 4.84 x 10(6) L/mol. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Ruthenium− and Osmium−Arene Complexes of 2-Substituted Indolo[3,2-<i>c</i>]quinolines: Synthesis, Structure, Spectroscopic Properties, and Antiproliferative Activity
  作者：Lukas K. Filak、Gerhard Mühlgassner、Felix Bacher、Alexander Roller、Mathea Sophia Galanski、Michael A. Jakupec、Bernhard K. Keppler、Vladimir B. Arion

  DOI：10.1021/om101004z

  日期：2011.1.24

  The synthesis of new modified indolo[3,2-c]quinoline ligands L-1-L-8 with metal-binding sites is reported. By coordination to ruthenium- and osmium-arene moieties 16 complexes of the type [(eta(6)-p-cymene)M(L)Cl]Cl (1a,b-8a,b), where M is Ru-II or Os-II and L is L-1-L-8, have been prepared. All compounds were comprehensively characterized by elemental analysis, electrospray ionization mass spectrometry, IR, UV-vis, and NMR spectroscopy, thermogravimetric analysis, and single-crystal X-ray diffraction (2a, 4a, 4b, 5a, 7a, and 7b). The complexes were tested for antiproliferative activity in vitro in three human cancer cell lines, namely, CH1 (ovarian carcinoma), SW480 (colon adenocarcinoma), and A549 (non-small-cell lung cancer), yielding IC50 values in the submicromolar or low micromolar range.