4-chloro-8-(2-nitrophenyl)-1,5-diazaanthracene-9,10-dione | 191849-09-9

• 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-chloro-8-(2-nitrophenyl)-1,5-diazaanthracene-9,10-dione
• 英文别名: 4-chloro-9-(2'-nitrophenyl)pyrido[2,3-g]-quinoline-5,10-dione；4-chloro-8-(o-nitrophenyl)-1,5-diazaanthraquinone；Pyrido[2,3-g]quinoline-5,10-dione, 4-chloro-9-(2-nitrophenyl)-；4-chloro-9-(2-nitrophenyl)pyrido[2,3-g]quinoline-5,10-dione
• CAS: 191849-09-9
• 化学式: C₁₈H₈ClN₃O₄
• 分子量: 365.732
• InChiKey: RDKCBRISAKGWLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  106
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-chloro-8-(2-nitrophenyl)-1,5-diazaanthracene-9,10-dione 在 palladium on activated charcoal sodium azide 、 氢气 作用下， 以 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 9-aminobenzo[b]pyrido[4,3,2-de][1,10]phenanthrolin-8(8H)-one
  参考文献：
  名称：

  Synthesis of cystodamine, a pentacyclic aza-aromatic alkaloid

  摘要：

  A pentacyclic aza-aromatic alkaloid, cystodamine (6), and its isomer (11) were synthesized from 7-(or 6-)bromo-4-chloro-5,8-quinolinedione (1, 8) and o-nitrocinnamaldehyde dimethylhydrazone (2) using hetero Diels-Alder reaction. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00926-x
• 作为产物：
  描述：

  (E)-3-(2-Nitrophenyl)propenal N,N-dimethylhydrazone 、 6-bromo-4-chloro-5,8-quinolinedione 在 乙酸酐 作用下， 以 氯仿 为溶剂， 反应 45.0h， 以27.6%的产率得到4-chloro-8-(2-nitrophenyl)-1,5-diazaanthracene-9,10-dione
  参考文献：
  名称：

  Synthesis of cystodamine, a pentacyclic aza-aromatic alkaloid

  摘要：

  A pentacyclic aza-aromatic alkaloid, cystodamine (6), and its isomer (11) were synthesized from 7-(or 6-)bromo-4-chloro-5,8-quinolinedione (1, 8) and o-nitrocinnamaldehyde dimethylhydrazone (2) using hetero Diels-Alder reaction. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00926-x

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。
• Cytotoxic compounds: derivatives of the pyrido [2,3,4-kl]acridine ring system
  申请人：Universidad Complutense de madrid

  公开号：US20020128281A1

  公开（公告）日：2002-09-12

  Compounds of formula (I), wherein X is selected from the group consisting of O, and NR 3 , where R 3 represents a lower alkyl group; Y is selected from the group consisting of CH and N; R 1 and R 2 are independently selected from the group consisting of NH 2 , NHR 4 and NR 5 2 , where R 4 and R 5 each represent a lower alkyl group, or R 1 and R 2 together represent a cycle selected from (a), (b) and (c), wherein R 6 , R 7 and R 8 are independently selected from the group consisting of hydrogen atoms, lower alkyl groups, hydroxy groups and lower alkoxy groups; and Z is selected from the group consisting of O.

  式（I）的化合物，其中X从O和NR3组成的组中选择，其中R3代表较低的烷基基团；Y从CH和N组成的组中选择；R1和R2分别从NH2、NHR4和NR52组成的组中独立选择，其中R4和R5各自代表较低的烷基基团，或者R1和R2一起代表从(a)、(b)和(c)中选择的环，其中R6、R7和R8从氢原子、较低的烷基基团、羟基和较低的烷氧基组成的组中独立选择；Z从O组成的组中选择。
• 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.
• CYTOTOXIC COMPOUNDS: DERIVATIVES OF THE PYRIDO 2,3,4-$i(kl)] ACRIDINE RING SYSTEM
  申请人：UNIVERSIDAD COMPLUTENSE DE MADRID

  公开号：EP0980372A2

  公开（公告）日：2000-02-23