6,8,9-trimethyl-11H-indolo<3,2-c>quinoline | 149429-22-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6,8,9-trimethyl-11H-indolo<3,2-c>quinoline
• 英文别名: 6,8,9-trimethyl-11H-indolo[3,2-c]quinoline
• CAS: 149429-22-1
• 化学式: C₁₈H₁₆N₂
• 分子量: 260.338
• InChiKey: DISDWAOVQQELPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6,8,9-trimethyl-11H-indolo<3,2-c>quinoline 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 生成 2,3-diethyl-12,13-dimethyl-10H-indolo<3,2-c>pyridazino<1,6-a>quinolin-5-inium mesitylenesulfonate
  参考文献：
  名称：

  Novel DNA Intercalators Based on the Pyridazino[1‘,6‘:1,2]pyrido[4,3-b]indol-5-inium System

  摘要：

  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.

  DOI：

  10.1021/jo982216d
• 作为产物：
  描述：

  5,6-二甲基-1H-苯并三唑水合物 在 焦磷酸 作用下， 反应 0.5h， 生成 6,8,9-trimethyl-11H-indolo<3,2-c>quinoline
  参考文献：
  名称：

  Synthesis and DNA Binding Properties of γ-Carbolinium Derivatives and Benzologues

  摘要：

  The 5H-pyrido[4,3-b]indole, 11H-indolo[3,2-c]quinoline, 5H-benzo[f]pyrido[4,3-b]indole, and 13H-benz[5,6]indolo[3,2-c]quinoline heteroaromatic nuclei have been synthesized by the Graebe-Ullmann method by classical heating or under microwave irradiation. These tri-, tetra-, and pentacyclic compounds were transformed into the corresponding cationic derivatives by N-alkylation, and the DNA-binding properties of the resulting cationic systems were examined using UV-vis spectroscopy, viscometric determinations, and molecular modeling techniques. The tetracyclic cations were transformed into his-salts by means of a diethyl bispiperidine rigid chain and a more flexible polyamide linker, but the low solubility of these bis-salts made the study of their bisintercalating properties difficult.

  DOI：

  10.1021/jo960266h

文献信息

• One-pot Graebe-Ullmann synthesis of γ-carbolines under microwave irradiation
  作者：Andrés Molina、Juan J. Vaquero、José L. García-Navio、Julio Alvarez-Builla

  DOI：10.1016/s0040-4039(00)77653-2

  日期：1993.4

  One-pot efficient and simple synthesis of γ-carboline derivatives by the Graebe-Ullmann method was conducted in a commercial microwave oven in a few minutes at a low energy level and using erlenmeyer as adequate reaction vessels. Yields are similar to those obtained by conventional heating.

  通过Graebe-Ullmann方法一锅高效，简单地合成γ-咔啉衍生物是在商用微波炉中以低能级在几分钟内以锥形瓶作为适当的反应容器进行的。产率类似于通过常规加热获得的产率。
• 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.
• Synthesis and DNA Binding Properties of γ-Carbolinium Derivatives and Benzologues
  作者：Andrés Molina、Juan J. Vaquero、José L. Garcia-Navio、Julio Alvarez-Builla、Beatriz de Pascual-Teresa、Federico Gago、María M. Rodrigo、Milagros Ballesteros

  DOI：10.1021/jo960266h

  日期：1996.1.1

  The 5H-pyrido[4,3-b]indole, 11H-indolo[3,2-c]quinoline, 5H-benzo[f]pyrido[4,3-b]indole, and 13H-benz[5,6]indolo[3,2-c]quinoline heteroaromatic nuclei have been synthesized by the Graebe-Ullmann method by classical heating or under microwave irradiation. These tri-, tetra-, and pentacyclic compounds were transformed into the corresponding cationic derivatives by N-alkylation, and the DNA-binding properties of the resulting cationic systems were examined using UV-vis spectroscopy, viscometric determinations, and molecular modeling techniques. The tetracyclic cations were transformed into his-salts by means of a diethyl bispiperidine rigid chain and a more flexible polyamide linker, but the low solubility of these bis-salts made the study of their bisintercalating properties difficult.