3-[2-(dimethylamino)ethylamino]acenaphtho[1,2-b]pyrazine-8,9-dicarbonitrile | 1232206-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[2-(dimethylamino)ethylamino]acenaphtho[1,2-b]pyrazine-8,9-dicarbonitrile
• 英文别名: 4-[2-(dimethylamino)ethylamino]-11,14-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-1(16),2,4,6,8,10,12,14-octaene-12,13-dicarbonitrile
• CAS: 1232206-74-4
• 化学式: C₂₀H₁₆N₆
• 分子量: 340.387
• InChiKey: FSIFWUYMWXCPRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  88.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-溴萘乙基-1,2-二酮 以 甲乙醚 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 3-[2-(dimethylamino)ethylamino]acenaphtho[1,2-b]pyrazine-8,9-dicarbonitrile
  参考文献：
  名称：

  Novel acenaphthopyrazine derivatives as antitumor agents against MCF-7 cells: molecular synthesis, optical properties, and DNA-binding studies

  摘要：

  A series of novel acenaphthopyrazine derivatives was synthesized from acenaphthylene-1,2-dione via three steps, including bromination, cyclization, and SNArH reaction. These new compounds exhibited potential antiproliferative activity against MCF-7 cells in vitro, and 3-[2-(dimethylamino)ethylamino]acenaphtho[1,2-b]pyrazine-8,9-dicarbonitrile exhibited the highest activity (IC (50) = 4.60 mu M). DNA-binding experiments suggested that these derivatives bind to DNA through intercalation with intrinsic binding constants K all above 10(5) M-1. Optical property studies indicated that these compounds have long emission wavelength (lambda (em) > 560 nm), high quantum yields in toluene (I broken vertical bar(f) = 0.59 for 3-(morpholin-4-yl)acenaphtho[1,2-b]pyrazine-8,9-dicarbonitrile), and large Stokes shift (Delta S > 130 nm).

  DOI：

  10.1007/s00706-011-0653-9

文献信息

• Novel acenaphthopyrazine derivatives as antitumor agents against MCF-7 cells: molecular synthesis, optical properties, and DNA-binding studies
  作者：Junling Xing、Jingnan Cui、Shuang Wang、Jin Gao、Zhichao Zhang

  DOI：10.1007/s00706-011-0653-9

  日期：2012.2

  A series of novel acenaphthopyrazine derivatives was synthesized from acenaphthylene-1,2-dione via three steps, including bromination, cyclization, and SNArH reaction. These new compounds exhibited potential antiproliferative activity against MCF-7 cells in vitro, and 3-[2-(dimethylamino)ethylamino]acenaphtho[1,2-b]pyrazine-8,9-dicarbonitrile exhibited the highest activity (IC (50) = 4.60 mu M). DNA-binding experiments suggested that these derivatives bind to DNA through intercalation with intrinsic binding constants K all above 10(5) M-1. Optical property studies indicated that these compounds have long emission wavelength (lambda (em) > 560 nm), high quantum yields in toluene (I broken vertical bar(f) = 0.59 for 3-(morpholin-4-yl)acenaphtho[1,2-b]pyrazine-8,9-dicarbonitrile), and large Stokes shift (Delta S > 130 nm).