methyl 8-bromo-6,11-dihydro-5H-pyrido[3,2-a]carbazole-2-carboxylate | 1632165-89-9

• 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: methyl 8-bromo-6,11-dihydro-5H-pyrido[3,2-a]carbazole-2-carboxylate
• CAS: 1632165-89-9
• 化学式: C₁₇H₁₃BrN₂O₂
• 分子量: 357.206
• InChiKey: WQWOBCDFICVHKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 8-bromo-6,11-dihydro-5H-pyrido[3,2-a]carbazole-2-carboxylate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 4.0h， 以81%的产率得到methyl 8-bromo-11H-pyrido[3,2-a]carbazole-2-carboxylate
  参考文献：
  名称：

  Synthetic Access to Poly-Substituted 11H-Pyrido[3,2-a]carbazoles, a DNA-Intercalating Ellipticine Related Structure, and Their Antiproliferative Activity

  摘要：

  The facile procedure for the synthesis of the 11H-pyrido[3,2-a]carbazole structure involving the Fischer indole cyclization on tetrahydroquinolinones, available from enaminones and methyl 2-formyl-3-oxopropanoate, followed by the aromatization of the resulting 5,6-dihydro derivatives is described. This method allows for the introduction of substituents at C2, C6, and C8 to the scaffold by choice of the starting materials. In the biological testing, introduction of the phenyl group at C6 is significantly effective to improve the antiproliferative activity.

  DOI：

  10.3987/com-14-12994
• 作为产物：
  描述：

  Methyl 5-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylate 、 对溴苯肼 在 盐酸 、 溶剂黄146 作用下， 反应 5.0h， 以74%的产率得到methyl 8-bromo-6,11-dihydro-5H-pyrido[3,2-a]carbazole-2-carboxylate
  参考文献：
  名称：

  Synthetic Access to Poly-Substituted 11H-Pyrido[3,2-a]carbazoles, a DNA-Intercalating Ellipticine Related Structure, and Their Antiproliferative Activity

  摘要：

  The facile procedure for the synthesis of the 11H-pyrido[3,2-a]carbazole structure involving the Fischer indole cyclization on tetrahydroquinolinones, available from enaminones and methyl 2-formyl-3-oxopropanoate, followed by the aromatization of the resulting 5,6-dihydro derivatives is described. This method allows for the introduction of substituents at C2, C6, and C8 to the scaffold by choice of the starting materials. In the biological testing, introduction of the phenyl group at C6 is significantly effective to improve the antiproliferative activity.

  DOI：

  10.3987/com-14-12994

文献信息

• Synthetic Access to Poly-Substituted 11H-Pyrido[3,2-a]carbazoles, a DNA-Intercalating Ellipticine Related Structure, and Their Antiproliferative Activity
  作者：Tsutomu Inokuchi、Joanna Wietrzyk、Ming-Yu Wu、Elkhabiry Shaban、Marta Świtalska、Ning Wang、Miho Shimoda、Yusuke Mizutani、Zhen-Wu Mei、Hiroyuki Kawafuchi、Junzo Nokami、Xiao-Qi Yu、Megumi Yoshida

  DOI：10.3987/com-14-12994

  日期：——

  The facile procedure for the synthesis of the 11H-pyrido[3,2-a]carbazole structure involving the Fischer indole cyclization on tetrahydroquinolinones, available from enaminones and methyl 2-formyl-3-oxopropanoate, followed by the aromatization of the resulting 5,6-dihydro derivatives is described. This method allows for the introduction of substituents at C2, C6, and C8 to the scaffold by choice of the starting materials. In the biological testing, introduction of the phenyl group at C6 is significantly effective to improve the antiproliferative activity.