2-[2-(2-Dimethylamino-ethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-ylamino]-benzoic acid | 873062-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-[2-(2-Dimethylamino-ethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-ylamino]-benzoic acid
• 英文别名: 2-[[2-[2-(Dimethylamino)ethyl]-1,3-dioxobenzo[de]isoquinolin-6-yl]amino]benzoic acid；2-[[2-[2-(dimethylamino)ethyl]-1,3-dioxobenzo[de]isoquinolin-6-yl]amino]benzoic acid
• CAS: 873062-60-3
• 化学式: C₂₃H₂₁N₃O₄
• 分子量: 403.437
• InChiKey: AKVRWUYPCGHZMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  90
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[2-(2-Dimethylamino-ethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-ylamino]-benzoic acid 在 三氯氧磷 作用下， 反应 12.0h， 生成 8-Chloro-5-(2-dimethylamino-ethyl)-5,13-diaza-benzo[de]naphthacene-4,6-dione
  参考文献：
  名称：

  Novel DNA bis-intercalators of isoquinolino[4,5-bc]acridines: design, synthesis and evaluation of cytotoxic activity

  摘要：

  Mono- and dinuclear isoquinolino[4,5-bc]acridine derivatives were designed and facilely synthesized, their DNA-binding affinities and cytotoxic activities were evaluated. A4 induced unwinding of supercoiled plasmid pBR 322 DNA by (36 +/- 2)degrees while A6 induced that by (41 +/- 1)degrees, both of which were higher than the mono-analogue A1 ((19 +/- 2)degrees). A6 exhibited the highest in vitro antitumor, activity against human lung cancer cell (A549) and A4 was the most active one against murine leukemia cell (P388). DNA binding constant and molecular model indicated that both the length of linker chain and the distance of interchromophore were key impact factors for DNA binding affinity and biological activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.065
• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 在 copper(l) iodide 、 铜 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 2-[2-(2-Dimethylamino-ethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-ylamino]-benzoic acid
  参考文献：
  名称：

  Novel DNA bis-intercalators of isoquinolino[4,5-bc]acridines: design, synthesis and evaluation of cytotoxic activity

  摘要：

  Mono- and dinuclear isoquinolino[4,5-bc]acridine derivatives were designed and facilely synthesized, their DNA-binding affinities and cytotoxic activities were evaluated. A4 induced unwinding of supercoiled plasmid pBR 322 DNA by (36 +/- 2)degrees while A6 induced that by (41 +/- 1)degrees, both of which were higher than the mono-analogue A1 ((19 +/- 2)degrees). A6 exhibited the highest in vitro antitumor, activity against human lung cancer cell (A549) and A4 was the most active one against murine leukemia cell (P388). DNA binding constant and molecular model indicated that both the length of linker chain and the distance of interchromophore were key impact factors for DNA binding affinity and biological activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.065

文献信息

• Novel DNA bis-intercalators of isoquinolino[4,5-bc]acridines: design, synthesis and evaluation of cytotoxic activity
  作者：Peng Yang、Qing Yang、Xuhong Qian

  DOI：10.1016/j.tet.2005.09.065

  日期：2005.12

  Mono- and dinuclear isoquinolino[4,5-bc]acridine derivatives were designed and facilely synthesized, their DNA-binding affinities and cytotoxic activities were evaluated. A4 induced unwinding of supercoiled plasmid pBR 322 DNA by (36 +/- 2)degrees while A6 induced that by (41 +/- 1)degrees, both of which were higher than the mono-analogue A1 ((19 +/- 2)degrees). A6 exhibited the highest in vitro antitumor, activity against human lung cancer cell (A549) and A4 was the most active one against murine leukemia cell (P388). DNA binding constant and molecular model indicated that both the length of linker chain and the distance of interchromophore were key impact factors for DNA binding affinity and biological activity. (c) 2005 Elsevier Ltd. All rights reserved.