4,9-diethyl-3,8-dimethylpyrido[2,3-g]quinoline-5,10-dione

• 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: 4,9-diethyl-3,8-dimethylpyrido[2,3-g]quinoline-5,10-dione
• 英文别名: 4,8-diethyl-3,7-dimethyl-1,5-diazaanthraquinone
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: YOVFDUZIDAIROP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,5-二溴-1,4-苯醌 、 2-Methyl-2-pentenal dimethyl-hydrazone 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.02h， 以70%的产率得到4,9-diethyl-3,8-dimethylpyrido[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

• 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 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.
• ANTITUMOUR 1,5-DIAZAANTHRAQUINONES
  申请人：UNIVERSIDAD COMPLUTENSE DE MADRID

  公开号：EP1080090A1

  公开（公告）日：2001-03-07
• US6525063B2
  申请人：——

  公开号：US6525063B2

  公开（公告）日：2003-02-25
• [EN] ANTITUMOUR 1,5-DIAZAANTHRAQUINONES<br/>[FR] 1,5-DIAZAANTHRAQUINONES ANTITUMORALES
  申请人：UNIV MADRID COMPLUTENSE

  公开号：WO1999059996A1

  公开（公告）日：1999-11-25

  Compounds having formula (I) wherein R?3, R4, R7, and R8¿ are independently selected from the group consisting of hydrogen, lower alkyl, halogen, amine, mono(lower)alkylamine, di(lower)alkylamine, phenyl, or substituted phenyl possess antitumour activity and are new with the exception of the compound in which R?3, R4, R7, R8¿ are all hydrogen and the compound in which R?3 and R7¿ are hydrogen, R4 is chlorine, and R8 is a 2-nitrophenyl group.