4-Hydroxy-9-(2-nitro-phenyl)-pyrido[2,3-g]quinoline-5,10-dione | 362050-99-5

• 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: 4-Hydroxy-9-(2-nitro-phenyl)-pyrido[2,3-g]quinoline-5,10-dione
• 英文别名: 4-(2-nitrophenyl)-6H-pyrido[2,3-g]quinoline-5,9,10-trione
• CAS: 362050-99-5
• 化学式: C₁₈H₉N₃O₅
• 分子量: 347.287
• InChiKey: OLVWOTMODPKMJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 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：
  122
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-9-(2-nitro-phenyl)-pyrido[2,3-g]quinoline-5,10-dione 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以19%的产率得到9-hydroxyisoascididemin
  参考文献：
  名称：

  A C-Ring Regioisomer of the Marine Alkaloid Meridine Exhibits Selective In Vitro Cytotoxicity for Solid Tumours

  摘要：

  9-Hydroxybenzo[b]pyrido[4,3,2-de](1,10)-phenantrolin-8-one (1), a regioisomer of the marine alkaloid meridine, was synthesized from 5,8-dimethoxy-6-nitro-4(1H)-quinolinone in eight steps and 23% overall yield. A shorter route was also investigated, based on the hetero Diels-Alder reaction between o-nitrocinnamaldehyde dimethylhydrazone and 4-halogen-6-bromo-5,8-quinolinequinones followed by reductive cyclization onto the C-5 carbonyl of the quinone. Compound 1 showed a remarkable in vitro cytotoxicity, with a pattern of selectivity towards solid rumours that is not found in the reference alkaloid, the activity against the human lung carcinoma (A-549) being particularly noteworthy. The activities of meridine and compound 1 as inhibitors of topoisomerase II were also significantly different. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00078-5
• 作为产物：
  描述：

  三甲基-(2-硝基苯基)锡烷 在 盐酸 、 四(三苯基膦)钯 、 sodium azide 、 ammonium cerium(IV) nitrate 、 硫酸 、 copper(I) bromide 作用下， 以 1,4-二氧六环 、 甲醇 、 二苯醚 、 水 、 乙腈 为溶剂， 反应 14.25h， 生成 4-Hydroxy-9-(2-nitro-phenyl)-pyrido[2,3-g]quinoline-5,10-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of new 1,5-diazaanthraquinones with cytotoxic activity

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2004.09.021

文献信息

• 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.
• A C-Ring Regioisomer of the Marine Alkaloid Meridine Exhibits Selective In Vitro Cytotoxicity for Solid Tumours
  作者：Jesús Ángel de la Fuente、M Jesús Martı́n、M del Mar Blanco、Eva Pascual-Alfonso、Carmen Avendaño、J. Carlos Menéndez

  DOI：10.1016/s0968-0896(01)00078-5

  日期：2001.7

  9-Hydroxybenzo[b]pyrido[4,3,2-de](1,10)-phenantrolin-8-one (1), a regioisomer of the marine alkaloid meridine, was synthesized from 5,8-dimethoxy-6-nitro-4(1H)-quinolinone in eight steps and 23% overall yield. A shorter route was also investigated, based on the hetero Diels-Alder reaction between o-nitrocinnamaldehyde dimethylhydrazone and 4-halogen-6-bromo-5,8-quinolinequinones followed by reductive cyclization onto the C-5 carbonyl of the quinone. Compound 1 showed a remarkable in vitro cytotoxicity, with a pattern of selectivity towards solid rumours that is not found in the reference alkaloid, the activity against the human lung carcinoma (A-549) being particularly noteworthy. The activities of meridine and compound 1 as inhibitors of topoisomerase II were also significantly different. (C) 2001 Elsevier Science Ltd. All rights reserved.