2,3-diethyl-6,10,11-trimethyl-8H-pyridazino<1',6':1,2>pyrido<4,3-b>indol-5-inium mesitylenesulfonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,3-diethyl-6,10,11-trimethyl-8H-pyridazino<1',6':1,2>pyrido<4,3-b>indol-5-inium mesitylenesulfonate
• 英文别名: 4,5-Diethyl-8,14,15-trimethyl-6,11-diaza-7-azoniatetracyclo[8.7.0.02,7.012,17]heptadeca-1(17),2,4,7,9,11,13,15-octaene;2,4,6-trimethylbenzenesulfonate；4,5-diethyl-8,14,15-trimethyl-6,11-diaza-7-azoniatetracyclo[8.7.0.02,7.012,17]heptadeca-1(17),2,4,7,9,11,13,15-octaene;2,4,6-trimethylbenzenesulfonate
• 化学式: C₉H₁₁O₃S*C₂₁H₂₄N₃
• 分子量: 517.692
• InChiKey: LVIKQPMOYZOOJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  37
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  93
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4,6-三甲基苯磺酰羟胺 在 二正丁胺 作用下， 以 乙醇 为溶剂， 生成 2,3-diethyl-6,10,11-trimethyl-8H-pyridazino<1',6':1,2>pyrido<4,3-b>indol-5-inium mesitylenesulfonate
  参考文献：
  名称：

  Azonia derivatives of the γ-carboline system. A new class of DNA intercalators

  摘要：

  1-Methyl-gamma-carboline derivatives were transformed into the corresponding N-aminoazinium salts, which were condensed with 1,2-dicarbonyl compounds (Westphal reaction) to afford azonia derivatives with a bridgehead quaternary nitrogen atom. Some of them show DNA intercalating properties. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00243-0

文献信息

• Azonia derivatives of the γ-carboline system. A new class of DNA intercalators
  作者：Andrés Molina、Juan J. Vaquero、JoséL. García-Navio、Julio Alvarez-Builla、María M. Rodrigo、Obis Castaño、JoséL. de Andres

  DOI：10.1016/s0960-894x(96)00243-0

  日期：1996.7

  1-Methyl-gamma-carboline derivatives were transformed into the corresponding N-aminoazinium salts, which were condensed with 1,2-dicarbonyl compounds (Westphal reaction) to afford azonia derivatives with a bridgehead quaternary nitrogen atom. Some of them show DNA intercalating properties. Copyright (C) 1996 Elsevier Science Ltd
• Novel DNA Intercalators Based on the Pyridazino[1‘,6‘:1,2]pyrido[4,3-<i>b</i>]indol-5-inium System
  作者：Andrés Molina、Juan J. Vaquero、José L. Garcia-Navio、Julio Alvarez-Builla、Beatriz de Pascual-Teresa、Federico Gago、María M. Rodrigo

  DOI：10.1021/jo982216d

  日期：1999.5.1

  A new class of DNA intercalators based on the 8H-pyridazino[1',6':1,2]pyrido[4,3-b]indol-5-inium system in which the cationic nature of the chromophore is provided by a brigdehead quaternary nitrogen has been obtained. These cations along with 10H-indolo[3,2-c]pyridazino[1,6-a]quinolin-5-inium, 13H-dibenz[f,h]indolo[3',2':3,4]pyrido[1,2-b]cinnolin-10-inium, and 5H-acenaphtho[1',2: 3',4']pyridazino[1',6':1,2]pyrido[4,3-b]indol-8-inium were synthesized by the Westphal reaction of carbolinium derivatives with various 1,2-dicarbonyl compounds. When these tetra-, penta-, and heptacyclic heteroaromatic nuclei were evaluated as DNA intercalators using UV-vis spectroscopy, viscometric determinations, and unwinding angle determinations, we found that only the 8H-pyridazino[1',6':1,2]pyrido[4,3-b]indol-5-inium cations behaved as DNA intercalators. Molecular modeling studies allowed the preferred orientation of the intercalating chromophore within a CpG intercalation site to be explored and will provide help in the rational design of novel bis-intercalators based on these chromophores.