9-amino-2,3-dimethyl-6-(2-dimethylaminoethyl)-6H-indolo[2,3-b]quinoxaline hydrochloride | 1092940-71-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 9-amino-2,3-dimethyl-6-(2-dimethylaminoethyl)-6H-indolo[2,3-b]quinoxaline hydrochloride
• 英文别名: 2-(9-Amino-2,3-dimethylindolo[3,2-b]quinoxalin-6-yl)ethyl-dimethylazanium;chloride
• CAS: 1092940-71-0
• 化学式: C₂₀H₂₃N₅*ClH
• 分子量: 369.897
• InChiKey: TWYCUEZZUSGRFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.91
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-(2-(dimethylamino)ethyl)-2,3-dimethyl-6H-indolo[2,3-b]quinoxalin-9-amine 在 盐酸 作用下， 以 水 为溶剂， 以94%的产率得到9-amino-2,3-dimethyl-6-(2-dimethylaminoethyl)-6H-indolo[2,3-b]quinoxaline hydrochloride
  参考文献：
  名称：

  Interactions of Antiviral Indolo[2,3-b]quinoxaline Derivatives with DNA

  摘要：

  Here, we present the synthesis of five novel indoloquinoxaline derivatives and investigate the DNA binding properties of these monomeric as well as dimeric compounds using absorption, fluorescence, and linear dichroism. Several of the mono- and dicationic derivatives presented have previously demonstrated an excellent antiviral effect that is higher than already acknowledged agents against human cytomegalovirus (CMV), herpes simplex virus type 1 (HSV-1), and varicella-zoster virus (VZV). We find that the DNA binding constants of the monomeric and dimeric derivatives are high (similar to 10(6)) and very high (similar to 10(9)) respectively. Results from the spectroscopic measurements show that the planar aromatic indoloquinoxaline moieties upon interaction with DNA intercalate between the nucleobases. Furthermore, we use poly(dA-dT)(2) and calf thymus DNA in a competitive binding experiment to show that all our derivatives have an wAT-region preference. The findings are important in the understanding of the antiviral effect of these derivatives and give invaluable information for the future optimization of the DNA binding properties of this kind of drugs.

  DOI：

  10.1021/jm800787b