2-(2,3-dimethyl-9-nitro-6H-indolo[2,3-b]quinoxalin-6-yl)-N,N-dimethylethanamine | 180208-81-5

• 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: 2-(2,3-dimethyl-9-nitro-6H-indolo[2,3-b]quinoxalin-6-yl)-N,N-dimethylethanamine
• 英文别名: 2,3-dimethyl-6-(2-dimethylaminoethyl)-9-nitro-6H-indolo[2,3-b]quinoxaline；2,3-dimethyl-6(2-dimethylaminoethyl)-9-nitro-6H-indolo[2,3-b]-quinoxaline；2-(2,3-dimethyl-9-nitroindolo[3,2-b]quinoxalin-6-yl)-N,N-dimethylethanamine
• CAS: 180208-81-5
• 化学式: C₂₀H₂₁N₅O₂
• 分子量: 363.419
• InChiKey: VJUUGOWHYDVBLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 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：
  79.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2,3-dimethyl-9-nitro-6H-indolo[2,3-b]quinoxalin-6-yl)-N,N-dimethylethanamine 在 palladium on activated charcoal 、 氢气 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 生成 6-(2-(dimethylamino)ethyl)-2,3-dimethyl-6H-indolo[2,3-b]quinoxalin-9-amine
  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
• 作为产物：
  描述：

  2,3-dimethyl-6-(N,N-dimethylaminoethyl)-6H-indolo(2,3-b)quinoxaline 在 硫酸 、 potassium nitrate 作用下， 生成 2-(2,3-dimethyl-9-nitro-6H-indolo[2,3-b]quinoxalin-6-yl)-N,N-dimethylethanamine
  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

文献信息

• Uses of indolo-(2,3b)-quinoxalines
  申请人：Lundbald Leif J. I.

  公开号：US06248742B1

  公开（公告）日：2001-06-19

  Use of compounds of the formula I for preparing a medicated for protecting DNA in the initial phase and/or the prompting phase of carcinogenesis and for preventing oxidating stress in patients with diseases related to free radicals are described.

  本发明涉及一种使用式I化合物制备药物的方法，用于保护DNA在癌症发生的初期和/或促进期，并预防与自由基相关的疾病患者的氧化应激。
• Uses of indolo-2 [2,3b] -quinoxalines
  申请人：Lundblad Leif J. I.

  公开号：US06465466B1

  公开（公告）日：2002-10-15

  Use of compounds of the formula I for preparing a medicament for protecting DNA in the initial phase and/or the promoting phase of carcinogenesis and for preventing oxidative stress in patients with diseases related to free radicals are described.

  本发明描述了使用I式化合物制备药物，用于保护DNA在癌症发展的初期和/或促进期以及预防与自由基相关的疾病患者的氧化应激。
• NEW USES OF INDOLO- 2,3b]-QUINOXALINES
  申请人：Lundblad, Leif J., I.

  公开号：EP0799038A1

  公开（公告）日：1997-10-08
• NEW USES OF INDOLO-[2,3b]-QUINOXALINES
  申请人：Lundblad, Leif J., I.

  公开号：EP0799038B1

  公开（公告）日：2001-09-05
• US6248742B1
  申请人：——

  公开号：US6248742B1

  公开（公告）日：2001-06-19