6,9-dihydroxy-11H-indeno[1,2-c]quinolin-11-one | 1135231-61-6

• 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: 6,9-dihydroxy-11H-indeno[1,2-c]quinolin-11-one
• 英文别名: 9-hydroxy-5H-indeno[1,2-c]quinoline-6,11-dione
• CAS: 1135231-61-6
• 化学式: C₁₆H₉NO₃
• 分子量: 263.252
• InChiKey: FXTKAGYTXYQNHN-UHFFFAOYSA-N

物化性质

• 沸点：
  616.9±55.0 °C(predicted)
• 密度：
  1.55±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,9-dihydroxy-11H-indeno[1,2-c]quinolin-11-one 、 3-溴丙烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以21%的产率得到6,9-bis(allyloxy)-11H-indeno[1,2-c]quinolin-11-one
  参考文献：
  名称：

  Discovery of Indeno[1,2-c]quinoline Derivatives as Inhibitors of Osteoclastogenesis Induced by Receptor Activator of NF-κB Ligand (RANKL)

  摘要：

  Certain indeno[1,2-c]quinolines were synthesized and evaluated for antiosteoclastogenic activities. Among them, 6,9-dimethoxy-11H-indeno[1,2-c]quinolin-11-one (8a) and 9-methoxy-6-(methylthio)-11H-indeno[1,2-c]quinolin-11-one (16a) inhibited RANKL-induced osteoclast formation in Raw 264.7 cells with an IC50 of 2.00 and 2.58 mu M, respectively. Compound 8a was only weakly active in the inhibition of the: RANKL-induced NFAT activation; while 16a was inactive. These results indicated that the antiosteoclastogenic effect of 8a is only; partly related while 16a is not related to the suppression of NFAT.

  DOI：

  10.1021/jm1016494
• 作为产物：
  描述：

  6-chloro-9-methoxy-11H-indeno[1,2-c]quinolin-11-one 在 氢溴酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 48.0h， 以78%的产率得到6,9-dihydroxy-11H-indeno[1,2-c]quinolin-11-one
  参考文献：
  名称：

  Discovery of Indeno[1,2-c]quinoline Derivatives as Inhibitors of Osteoclastogenesis Induced by Receptor Activator of NF-κB Ligand (RANKL)

  摘要：

  Certain indeno[1,2-c]quinolines were synthesized and evaluated for antiosteoclastogenic activities. Among them, 6,9-dimethoxy-11H-indeno[1,2-c]quinolin-11-one (8a) and 9-methoxy-6-(methylthio)-11H-indeno[1,2-c]quinolin-11-one (16a) inhibited RANKL-induced osteoclast formation in Raw 264.7 cells with an IC50 of 2.00 and 2.58 mu M, respectively. Compound 8a was only weakly active in the inhibition of the: RANKL-induced NFAT activation; while 16a was inactive. These results indicated that the antiosteoclastogenic effect of 8a is only; partly related while 16a is not related to the suppression of NFAT.

  DOI：

  10.1021/jm1016494

文献信息

• Discovery of Indeno[1,2-<i>c</i>]quinoline Derivatives as Inhibitors of Osteoclastogenesis Induced by Receptor Activator of NF-κB Ligand (RANKL)
  作者：Chih-Hua Tseng、Ru-Wei Lin、Yeh-Long Chen、Gwo-Jaw Wang、Mei-Ling Ho、Cherng-Chyi Tzeng

  DOI：10.1021/jm1016494

  日期：2011.4.28

  Certain indeno[1,2-c]quinolines were synthesized and evaluated for antiosteoclastogenic activities. Among them, 6,9-dimethoxy-11H-indeno[1,2-c]quinolin-11-one (8a) and 9-methoxy-6-(methylthio)-11H-indeno[1,2-c]quinolin-11-one (16a) inhibited RANKL-induced osteoclast formation in Raw 264.7 cells with an IC50 of 2.00 and 2.58 mu M, respectively. Compound 8a was only weakly active in the inhibition of the: RANKL-induced NFAT activation; while 16a was inactive. These results indicated that the antiosteoclastogenic effect of 8a is only; partly related while 16a is not related to the suppression of NFAT.