2-苯基喹啉-5,8-二酮 | 146830-22-0

• 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
• 中文名称: 2-苯基喹啉-5,8-二酮
• 英文名称: 2-phenylquinoline-5,8-quinone
• 英文别名: 2-phenylquinoline-5,8-dione
• CAS: 146830-22-0
• 化学式: C₁₅H₉NO₂
• 分子量: 235.242
• InChiKey: DUEZCRDGVOANPB-UHFFFAOYSA-N

物化性质

• 沸点：
  459.4±45.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-苯基喹啉-5,8-二酮 在 盐酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.18h， 生成 6-(2-Chloroethylamino)-2-phenylquinoline-5,8-dione
  参考文献：
  名称：

  Design of quinolinedione-Based geldanamycin analogues

  摘要：

  Quinoline-5,8-dione-based compounds were designed from the structure of the geldanamycin-bound Hsp-90 active site. The active site model predicted that aromatic substituents should be present at the 2-position, to take advantage of a hydrophobic pocket, and amino substituents should be present at the 6- or 7-position. COMPARE analysis revealed that the LC50 profile of 2-phenyl-6-(2-chloroethylamino)quinoline-5,8-dione has the highest geldanamycin-like activity (0.74 correlation coefficient). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00650-4
• 作为产物：
  描述：

  3,6-二甲氧基-2-硝基苯甲醛 在 吡啶-2,6-二羧酸 n-氧化物 、 盐酸 、 氢氧化钾 、 ammonium cerium(IV) nitrate 、 铁粉 作用下， 以 乙醇 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 19.25h， 生成 2-苯基喹啉-5,8-二酮
  参考文献：
  名称：

  Incorporation of the quinoline-5,8-quinone moiety into polyaza cavities

  摘要：

  Silica gel supported nitric acid treatment of 2,5-dimethoxybenzaldehyde followed by reduction with iron powder provides 3,6-dimethoxy-2-aminobenzaldehyde. Friedlander condensation of this species with a variety of ketones and diketones leads to 5,8-dimethoxyquinoline derivatives which may be oxidized by ceric ammonium nitrate (CAN) and pyridine-2,6-dicarboxylic acid N-oxide (PDANO) to the corresponding quinones. The quinone functionality can be incorporated into larger cavities by a selective stepwise Friedlander approach and the CAN/PDANO oxidation appears to work preferentially for 5,8-dimethoxyquinoline.

  DOI：

  10.1021/jo00059a012

文献信息

• Novel quinolinequinone antitumor agents: structure-metabolism studies with NAD(P)H:quinone oxidoreductase (NQO1)
  作者：Tara Fryatt、Hanna I Pettersson、Walter T Gardipee、Kurtis C Bray、Stephen J Green、Alexandra M.Z Slawin、Howard D Beall、Christopher J Moody

  DOI：10.1016/j.bmc.2004.01.021

  日期：2004.4

  For aromatic substituents, the rate of reduction decreases dramatically for R(2)=Ph>1-naphthyl>2-naphthyl>4-biphenyl. Compounds containing a pyridine substituent are the best substrates, and the rates decrease as R(2)=4-pyridyl>3-pyridyl>2-pyridyl>4-methyl-2-pyridyl>5-methyl-2-pyridyl. The toxicity toward human colon carcinoma cells with either no detectable activity (H596 or BE-WT) or high NQO1 activity

  合成了一系列带有各种取代基的喹啉醌，研究了取代基对重组人NAD（P）H：醌氧化还原酶（hNQO1）代谢的影响。选择了一系列喹啉醌进行研究，并经过专门设计以探测C-2处芳基取代基的作用。使用三种常规策略制备了28种喹啉醌2-29，它们分别是：钯（0）催化的2-氯喹啉偶联，经典的弗里德兰德合成和对乙酰苯胺的双维尔斯迈尔反应。还制备了异喹啉醌30的一个实例，并通过循环伏安法测量了醌的还原电势。对于在喹啉2位的简单取代基R（2），对于R（2）= Cl>，由hNQO1引起的醌代谢速率降低 H大约Me> Ph。对于芳族取代基，对于R（2）＝ Ph> 1-萘基> 2-萘基> 4-联苯，还原速率显着降低。含有吡啶取代基的化合物是最好的底物，且比率随着R（2）= 4-吡啶基> 3-吡啶基> 2-吡啶基> 4-甲基-2-吡啶基> 5-甲基-2-吡啶基而降低。在代表醌中还研究了对人结肠癌细胞的毒性，该细胞既无可
• Discovery of Quinolinediones Exhibiting a Heat Shock Response and Angiogenesis Inhibition
  作者：Robert H. J. Hargreaves、Cynthia L. David、Luke J. Whitesell、Daniel V. LaBarbera、Akmal Jamil、Jean C. Chapuis、Edward B. Skibo

  DOI：10.1021/jm7014099

  日期：2008.4.1

  A series of substituted quinoline-5,8-diones were synthesized and evaluated as inhibitors of the chaperone protein Hsp90 using two assays: competition for binding to C-terminal ATP-binding site and competition for binding to N-terminal ATP-binding site. In addition, the ability of the compounds to induce the heat shock response was determined using a reporter fibroblast cell line. Of all the compounds assayed, only 6-aziridinyl-2-biphenylquinoline-5,8-dione induced a heat shock response and did so without interacting at the ATP binding sites of Hsp90. COMPARE analysis was carried out on quinoline-5,8-diones active in the National Cancer Institute's 60-cell line screen with the goal of discovering quinoline-5,8-dione structures that interact with other cellular targets (molecular targets) important for cancer chemotherapy. COMPARE analysis led to the discovery of a combretastatin- like quinoline-5,8-dione structure that, in fact, inhibited angiogenesis.
• Incorporation of the quinoline-5,8-quinone moiety into polyaza cavities
  作者：Randolph P. Thummel、Sara Chirayil、Christophe Hery、Jean Luc Lim、Tie Lin Wang

  DOI：10.1021/jo00059a012

  日期：1993.3

  Silica gel supported nitric acid treatment of 2,5-dimethoxybenzaldehyde followed by reduction with iron powder provides 3,6-dimethoxy-2-aminobenzaldehyde. Friedlander condensation of this species with a variety of ketones and diketones leads to 5,8-dimethoxyquinoline derivatives which may be oxidized by ceric ammonium nitrate (CAN) and pyridine-2,6-dicarboxylic acid N-oxide (PDANO) to the corresponding quinones. The quinone functionality can be incorporated into larger cavities by a selective stepwise Friedlander approach and the CAN/PDANO oxidation appears to work preferentially for 5,8-dimethoxyquinoline.
• Design of quinolinedione-Based geldanamycin analogues
  作者：Robert Hargreaves、Cynthia L. David、Luke Whitesell、Edward B. Skibo

  DOI：10.1016/s0960-894x(03)00650-4

  日期：2003.9

  Quinoline-5,8-dione-based compounds were designed from the structure of the geldanamycin-bound Hsp-90 active site. The active site model predicted that aromatic substituents should be present at the 2-position, to take advantage of a hydrophobic pocket, and amino substituents should be present at the 6- or 7-position. COMPARE analysis revealed that the LC50 profile of 2-phenyl-6-(2-chloroethylamino)quinoline-5,8-dione has the highest geldanamycin-like activity (0.74 correlation coefficient). (C) 2003 Elsevier Ltd. All rights reserved.