6-氨基-4-苯基喹啉-5,8-二酮 | 824405-24-5

• 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
• 中文名称: 6-氨基-4-苯基喹啉-5,8-二酮
• 英文名称: 6-Amino-4-phenylquinoline-5,8-dione
• 英文别名: 6-amino-4-phenylquinoline-5,8-dione
• CAS: 824405-24-5
• 化学式: C₁₅H₁₀N₂O₂
• 分子量: 250.257
• InChiKey: GZXIOPDZMROIEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 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：
  73
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-氨基-4-苯基喹啉-5,8-二酮 以 甲醇 、 二苯醚 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.42h， 生成 4-Methoxy-9-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
• 作为产物：
  描述：

  三甲基(苯基)锡 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 、 水 、 乙腈 为溶剂， 反应 8.5h， 生成 6-氨基-4-苯基喹啉-5,8-二酮
  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.