6-bromo-4-chloro-5,8-quinolinedione | 150222-05-2

• 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-bromo-4-chloro-5,8-quinolinedione
• 英文别名: 6-bromo-4-chloro-5,8-quinolinequinone；6-Bromo-4-chloroquinoline-5,8-dione
• CAS: 150222-05-2
• 化学式: C₉H₃BrClNO₂
• 分子量: 272.485
• InChiKey: SCEGLLOJIOXJCK-UHFFFAOYSA-N

物化性质

• 沸点：
  404.4±45.0 °C(Predicted)
• 密度：
  1.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• 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：

  6-bromo-4-chloro-5,8-quinolinedione 在 cerium(III) chloride 、 硫酸 、 氧气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 4-chloro-11-methylpyrido[2,3-b]acridine-5,12-dione
  参考文献：
  名称：

  五环芳族生物碱，宽氨胺A，11-羟基阿斯卡德明和乙酸新愈伤组织的合成研究

  摘要：

  五环芳族生物碱，宽胺碱A（6）分三步合成，分别由6-甲氧基苯并噻唑-4,7-二酮（8）和2-氨基苯乙酮（9）组成。由5，8-喹啉二酮（13、14）或1，4-ac啶二酮（20）制备11-羟基天冬酰胺（4）。醋酸neocalliactine的结构，calliactine的衍生物，被确定为5通过全合成从6-甲氧基-5,8-二quinolinedione（28）和2-氨基-5-甲氧基苯乙酮（29）。

  DOI：

  10.1016/s0040-4020(97)10153-3
• 作为产物：
  描述：

  6-bromo-4-chloro-5,8-dimethoxyquinoline 在 吡啶-2,6-二羧酸 n-氧化物 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以61%的产率得到6-bromo-4-chloro-5,8-quinolinedione
  参考文献：
  名称：

  4-氨基取代的6-羟基和11-羟基萘并[2,3- g ]喹啉-5,12-二酮的合成，以及意想不到的双取代的咪唑并[4,5，l-i，j ]萘并[ 2,3- g ]喹啉-7-ones

  摘要：

  使4-氯喹啉-5,8-二酮（8a）和6-溴-4-氯喹啉-5,8-二酮（8b）与高邻苯二甲酸酐反应，分别得到四环化合物10和11。通过将苯并环丁烯二酮光化学加到4-氯喹啉-5,8-二酮（8a）中以低收率制得6,11-二羟基衍生物12，并通过邻苯二甲酸酐与4-氯-5的Friedel-Crafts反应获得更好的收率。 ，8-二甲氧基喹啉（7a）。而4-氯-6-羟基萘并[2,3 - g ]喹啉-5,12-二酮（11）以通常的方式被胺取代为相应的4-氨基取代的衍生物4-氯-11-羟基萘-邻[2,3 - g ]喹啉-5,12-二酮（10），形成4-氨基衍生物和意外的2,6-二取代-咪唑并[4,5,1- Ij ]萘并[2,3- g ]喹啉-7-ones，13a-b。

  DOI：

  10.1002/jhet.5570300111

文献信息

• Antitumour 1,5-diazaanthraquinones
  申请人：——

  公开号：US20020099066A1

  公开（公告）日：2002-07-25

  1 Compounds having formula (I) wherein R 3 , R 4 , R 7 , and R 8 are independently selected from the group consisting of hydrogen, lower alkyl, halogen, amine, mono(lower)alkylamine, di(lower)alkylamine, phenyl, or substituted phenyl possess antitumor activity and are new with the exception of the compound in which R 3 , R 4 , R 7 , R 8 are all hydrogen and the compound in which R 3 and R 7 are hydrogen, R 4 chlorine, and R 8 is a 2-nitrophenyl group.

  具有公式(I)的化合物，其中R3、R4、R7和R8独立地选自包括氢、低级烷基、卤素、胺、单（低级）烷基胺、二（低级）烷基胺、苯基或取代苯基的组，具有抗肿瘤活性，除了R3、R4、R7、R8均为氢的化合物和R3和R7为氢，R4为氯，R8为2-硝基苯基的化合物外，都是新的。
• Synthesis of 4-Amino-substituted-6-hydroxy and 11-hydroxynaphtho[2,3-<i>g</i>]quinoline-5,12-diones, and the unexpected formation of disubstituted imidazo[4,5,l-<i>i,j</i>]naphtho[2,3-<i>g</i>]quinolin-7-ones
  作者：Martine Croisy-Delcey、Emile Bisagni、Christiane Huel

  DOI：10.1002/jhet.5570300111

  日期：1993.1

  8-dimethoxyquinoline (7a). Whereas 4-chloro-6-hydroxynaphtho[2,3-g]quinoline-5,12-dione (11) was substituted by amines in the usual way to the corresponding 4-amino-substituted derivatives, 4-chloro-11-hydroxynaph-tho[2,3-g]quinoline-5,12-dione (10) led to a mixture of 4-amino derivatives and the unexpected 2,6-disubstituted-imidazo[4,5,l-I-j]naphtho[2,3-g]quinolin-7-ones, 13a-b.

  使4-氯喹啉-5,8-二酮（8a）和6-溴-4-氯喹啉-5,8-二酮（8b）与高邻苯二甲酸酐反应，分别得到四环化合物10和11。通过将苯并环丁烯二酮光化学加到4-氯喹啉-5,8-二酮（8a）中以低收率制得6,11-二羟基衍生物12，并通过邻苯二甲酸酐与4-氯-5的Friedel-Crafts反应获得更好的收率。 ，8-二甲氧基喹啉（7a）。而4-氯-6-羟基萘并[2,3 - g ]喹啉-5,12-二酮（11）以通常的方式被胺取代为相应的4-氨基取代的衍生物4-氯-11-羟基萘-邻[2,3 - g ]喹啉-5,12-二酮（10），形成4-氨基衍生物和意外的2,6-二取代-咪唑并[4,5,1- Ij ]萘并[2,3- g ]喹啉-7-ones，13a-b。
• Synthesis and structure–activity relationships of 1,5-diazaanthraquinones as antitumour compounds
  作者：Carmen Avendaño、José Marı́a Pérez、Ma̱ del Mar Blanco、Jesús Ángel de la Fuente、Sonia Manzanaro、Marı́a Jesús Vicent、Marı́a Jesús Martı́n、Nélida Salvador-Tormo、J.Carlos Menéndez

  DOI：10.1016/j.bmcl.2004.05.055

  日期：2004.8

  1,5-Diazaanthraquinone derivatives were synthesized employing single and double hetero Diels-Alder strategies. Their in vitro antitumour activity was assayed using three cell lines. Some of these compounds, specially those bearing methyl or ethyl groups at the C-3,7 positions or chloro at C-4 and methyl at C-7, showed IC50 values in the 10(-8) M range for human lung carcinoma and human melanoma, which makes them attractive candidates for further development as anticancer agents. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of new 1,5-diazaanthraquinones with cytotoxic activity
  作者：Sonia Manzanaro、María Jesús Vicent、María Jesús Martín、Nélida Salvador-Tormo、José María Pérez、María del Mar Blanco、Carmen Avendaño、José Carlos Menéndez、Jesús Ángel de la Fuente

  DOI：10.1016/j.bmc.2004.09.021

  日期：2004.12

  series of 1,5-diazaanthraquinone derivatives was synthesized and their in vitro cytotoxic activities were evaluated against several human cancer cell lines. The 1,5-diazaanthraquinone chromophore has been synthesized either on the basis of hetero Diels-Alder reactions involving different quinoline-5,8-diones and alpha,beta,-unsaturated aldehyde N,N-dimethylhydrazones or by thertmolysis of different arylaminotnethylene Meldrntm's acid derivatives. Some of these compounds showed cytotoxic activity comparable to that of mitoxantrone against most of the cell lines tested. Compounds 20, 30, 31 and 37 were 4-54 times more potent that mitoxantrone against A549, H 116, PSN 1 and T98G cancer cell lines but, interestingly, they were 3-16 times less potent against the human breast carcinoma SKBR3. Some structure-activity relationships are described, the most significant one being the increase in cytotoxicity resulting from the introduction of a halogen atom at the C-4 position. (C) 2004 Elsevier Ltd. All rights reserved.
• Total Synthesis of Kuanoniamine A, 11-Hydroxyascididemin, and Neocalliactine Acetate
  作者：Yoshiyasu Kitahara、Shinsuke Nakahara、Takanobu Yonezawa、Masanori Nagatsu、Akinori Kubo

  DOI：10.3987/com-92-6321

  日期：——

  A pentacyclic aromatic alkaloid, kuanoniamine A (5) was synthesized from 6-methoxybenzothiazole-4,7-dione (7) and 2-aminoacetophenone (8). Similarly, 11-hydroxyascididemin (4) was prepared from 6-bromo-4-chloro-5,8-dimethoxyquinoline (12). The structure of neocalliactine acetate, a derivative of calliactine, was determined at 19 by total synthesis from 6-methoxy-5,8-quinolinedione (23) and 2-amino-5-methoxyacetophenone (24).