8-methoxy-11H-pyrido<3,2-a>carbazole | 102852-62-0

• 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: 8-methoxy-11H-pyrido<3,2-a>carbazole
• 英文别名: 8-methoxy-11H-pyrido[3,2-a]carbazole
• CAS: 102852-62-0
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: JQHYHMASUBHIKD-UHFFFAOYSA-N

物化性质

• 沸点：
  501.4±30.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-methoxy-11H-pyrido<3,2-a>carbazole 在 氢溴酸 作用下， 反应 5.0h， 以39.5%的产率得到8-hydroxy-11H-pyrido<3,2-a>carbazole
  参考文献：
  名称：

  Synthesis of 11H-pyridocarbazoles and derivatives. Comparison of their DNA binding and antitumor activity with those of 6H- and 7H-pyridocarbazoles

  摘要：

  The 8-methoxy- and 8-hydroxy-11H-pyrido[2,3-a]-, -[3,4-a]-, -[4,3-a]-, and [3,2-a]carbazoles were synthesized as potential DNA intercalating antitumor drugs. The structure of these compounds was confirmed by 1H NMR study including NOE experiments. The DNA binding properties of substituted and unsubstituted (8-H) heterocycles were determined by using their hydrochlorides or methiodides. These derivatives are able to bind to DNA with an affinity varying from 2.0 X 10(4) to 1.0 X 10(6) M-1, but most of them are unable to intercalate in contrast with the behavior of 6H- and 7H-pyridocarbazole analogues. The cytotoxicity of 11H-pyridocarbazoles, measured on L1210 cells in vitro, is much lower than those of 6H- and 7H-pyridocarbazole analogues.

  DOI：

  10.1021/jm00159a028
• 作为产物：
  描述：

  4-甲氧基环己酮 在 palladium on activated charcoal 硫酸 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 、 水 、 萘烷 为溶剂， 反应 8.75h， 生成 8-methoxy-11H-pyrido<3,2-a>carbazole
  参考文献：
  名称：

  Synthesis of 11H-pyridocarbazoles and derivatives. Comparison of their DNA binding and antitumor activity with those of 6H- and 7H-pyridocarbazoles

  摘要：

  The 8-methoxy- and 8-hydroxy-11H-pyrido[2,3-a]-, -[3,4-a]-, -[4,3-a]-, and [3,2-a]carbazoles were synthesized as potential DNA intercalating antitumor drugs. The structure of these compounds was confirmed by 1H NMR study including NOE experiments. The DNA binding properties of substituted and unsubstituted (8-H) heterocycles were determined by using their hydrochlorides or methiodides. These derivatives are able to bind to DNA with an affinity varying from 2.0 X 10(4) to 1.0 X 10(6) M-1, but most of them are unable to intercalate in contrast with the behavior of 6H- and 7H-pyridocarbazole analogues. The cytotoxicity of 11H-pyridocarbazoles, measured on L1210 cells in vitro, is much lower than those of 6H- and 7H-pyridocarbazole analogues.

  DOI：

  10.1021/jm00159a028