13H-benz<5,6>indolo<3,2-c>quinoline | 149429-24-3

• 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: 13H-benz<5,6>indolo<3,2-c>quinoline
• 英文别名: 13H-Benz(5,6)indolo(3,2-c)quinoline；12,20-diazapentacyclo[11.8.0.02,11.04,9.014,19]henicosa-1(13),2,4,6,8,10,14,16,18,20-decaene
• CAS: 149429-24-3
• 化学式: C₁₉H₁₂N₂
• 分子量: 268.318
• InChiKey: WCNKEWMBZFDYGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  13H-benz<5,6>indolo<3,2-c>quinoline 、 碘甲烷 以 乙腈 为溶剂， 反应 48.0h， 以78%的产率得到20-Methyl-12-aza-20-azoniapentacyclo[11.8.0.02,11.04,9.014,19]henicosa-1(13),2,4,6,8,10,14,16,18,20-decaene;iodide
  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
• 作为产物：
  描述：

  3-Quinolin-4-ylbenzo[f]benzotriazole 在 焦磷酸 作用下， 以64%的产率得到13H-benz<5,6>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。
• 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.