1,3-二甲基-5H-吡啶并(4,3-b)吲哚 | 46382-84-7

• 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
• 中文名称: 1,3-二甲基-5H-吡啶并(4,3-b)吲哚
• 英文名称: 1,3-dimethyl-5H-pyrido<4,3-b>indole
• 英文别名: 1,3-dimethyl-5H-pyrido[4,3-b]indole；1,3-Dimethyl-γ-carbolin；2,4-Dimethyl-γ-carbolin；1,3-dimethyl-5H-pyrido[4,3-b]indole
• CAS: 46382-84-7
• 化学式: C₁₃H₁₂N₂
• 分子量: 196.252
• InChiKey: LSMFRNHNKRLJLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1,3-二甲基-5H-吡啶并(4,3-b)吲哚 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 生成 2,3,6-trimethyl-8H-pyridazino<1',6':1,2>pyrido<4,3-b>indol-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：

  4-氯-2,6-二甲基吡啶 在 焦磷酸 作用下， 反应 0.5h， 生成 1,3-二甲基-5H-吡啶并(4,3-b)吲哚
  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

• 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.