10,11-dihydro-11-oxo-5H-indolo[3,2-b]quinoline-7-carboxylic acid | 1059624-30-4

• 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: 10,11-dihydro-11-oxo-5H-indolo[3,2-b]quinoline-7-carboxylic acid
• 英文别名: 11-oxo-10,11-dihydro-5H-indolo[3,2-b]quinolin-7-carboxylic acid；11-Oxo-5,10-dihydroindolo[3,2-b]quinoline-7-carboxylic acid
• CAS: 1059624-30-4
• 化学式: C₁₆H₁₀N₂O₃
• 分子量: 278.267
• InChiKey: AZKUARZSQPWXIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10,11-dihydro-11-oxo-5H-indolo[3,2-b]quinoline-7-carboxylic acid 在 palladium on activated charcoal 、 氢气 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 52.0h， 生成 10H-indolo[3,2-b]quinoline-7-carboxylic acid
  参考文献：
  名称：

  Synthesis, Saccharide-Binding and Anti-cancer Cell Proliferation Properties of Arylboronic Acid Derivatives of Indoquinolines

  摘要：

  A facile synthesis of a series of saccharide‐binding arylboronic acid derivatives of indoloquinoline was described. The key synthetic steps were polyphosphoric acid‐mediated cyclization, chlorinative aromatization, and amidation. Mass spectrometry experiments revealed these synthetic arylboronic acid derivatives of indoquinolines could bind to biologically important carbohydrates (sialic acid, fucose, glucose, and galactose) by forming boronate di‐esters in alkaline aqueous solution. Most of the arylboronic acid derivatives of indoquinolines inhibited human breast cancer cell (MDA–231) proliferation at a concentration of 5 μm, whereas the compound 17 exhibited highest percentages (76.74%) of the cancer cell proliferation inhibition.

  DOI：

  10.1111/j.1747-0285.2011.01196.x
• 作为产物：
  描述：

  2-chloroacetamidobenzoic acid 在 碳酸氢钠 、 sodium hydrogensulfite 作用下， 以 水 为溶剂， 反应 28.0h， 生成 10,11-dihydro-11-oxo-5H-indolo[3,2-b]quinoline-7-carboxylic acid
  参考文献：
  名称：

  新型降血脂素类似物的合成及其对肿瘤细胞的细胞毒性

  摘要：

  设计并合成了六种新颖的生物活性天然吲哚并[3,2- b ]喹啉生物碱苷芥子油苷，采用多磷酸介导的环化作用和两种不同的酰胺化策略，将四-O-乙酰-β - d-葡糖胺引入四环羧酸酸。

  DOI：

  10.1002/jhet.2381

文献信息

• Synthesis, G-Quadruplex Stabilisation, Docking Studies, and Effect on Cancer Cells of Indolo[3,2-<i>b</i>]quinolines with One, Two, or Three Basic Side Chains
  作者：João Lavrado、Pedro M. Borralho、Stephan A. Ohnmacht、Rui E. Castro、Cecília M. P. Rodrigues、Rui Moreira、Daniel J. V. A. dos Santos、Stephen Neidle、Alexandra Paulo

  DOI：10.1002/cmdc.201300288

  日期：2013.8.19

  binding and G4 DNA thermal stabilisation increase with an N5‐methyl or a 7‐carboxylate group and propylamine side chains, whereas selectivity between G4 and duplex DNA appears to be modulated by the number and relative position of basic side chains. From all the indoloquinoline derivatives studied, the novel trisubstituted compounds 3 d and 4 d, bearing a 7‐(aminoalkyl)carboxylate side chain, stand out

  端粒和致癌启动子区域中的G-四链体（G4）DNA结构是癌症治疗的潜在目标，并且已证明G4配体可调节端粒酶活性和癌基因转录。在这里，我们报告了20种吲哚[3,2- b]的合成和G4热稳定作用，通过FRET熔解测定确定]喹啉单，双和三取代有碱性侧链。还进行了分子建模研究，以试图使配体与G4的结合姿势合理化。总体而言，结果表明配体结合和G4 DNA热稳定性随N5-甲基或7-羧基和丙胺侧链而增加，而G4和双链DNA之间的选择性似乎受碱性侧基的数量和相对位置的调节链。在所有研究过的吲哚喹啉衍生物中，带有7-（氨基烷基）羧酸酯侧链的新型三取代化合物3 d和4 d脱颖而出，是最有希望的化合物。它们显示出较高的G4热稳定性（ΔT m值在17至8°C之间），且G4间的ΔHsp90A > KRas21R≈F21T > c-Kit2的T m趋势，对G4的选择性比双链DNA高10倍，对HCT116癌细胞系（IC 50和IC
• Synthesis, Saccharide-Binding and Anti-cancer Cell Proliferation Properties of Arylboronic Acid Derivatives of Indoquinolines
  作者：Junxiu Meng、Shaoqing Yu、Shengbiao Wan、Sumei Ren、Tao Jiang

  DOI：10.1111/j.1747-0285.2011.01196.x

  日期：2011.11

  A facile synthesis of a series of saccharide‐binding arylboronic acid derivatives of indoloquinoline was described. The key synthetic steps were polyphosphoric acid‐mediated cyclization, chlorinative aromatization, and amidation. Mass spectrometry experiments revealed these synthetic arylboronic acid derivatives of indoquinolines could bind to biologically important carbohydrates (sialic acid, fucose, glucose, and galactose) by forming boronate di‐esters in alkaline aqueous solution. Most of the arylboronic acid derivatives of indoquinolines inhibited human breast cancer cell (MDA–231) proliferation at a concentration of 5 μm, whereas the compound 17 exhibited highest percentages (76.74%) of the cancer cell proliferation inhibition.
• Synthesis of Novel Jusbetonin Analogues and Their Cytotoxicity against Tumor Cell
  作者：Shixu Liu、Junxiu Meng、Wei Zhang、Shengbiao Wan、Tao Jiang

  DOI：10.1002/jhet.2381

  日期：2016.7

  Six novel analogues of bioactive natural indolo[3,2‐b]quinoline alkaloid glycoside jusbetonin were designed and synthesized, employing polyphosphoric acid mediated cyclization and two different amidation strategies on introduction of tetra‐O‐acetyl‐β‐d‐glucosamine to tetracyclic carboxylic acids.

  设计并合成了六种新颖的生物活性天然吲哚并[3,2- b ]喹啉生物碱苷芥子油苷，采用多磷酸介导的环化作用和两种不同的酰胺化策略，将四-O-乙酰-β - d-葡糖胺引入四环羧酸酸。