11-hydroxy-6-methyl-11H-indeno[1,2-c]isoquinolin-5-one | 958008-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 11-hydroxy-6-methyl-11H-indeno[1,2-c]isoquinolin-5-one
• CAS: 958008-18-9
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: CGBWHDVBRQFKIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11-hydroxy-6-methyl-11H-indeno[1,2-c]isoquinolin-5-one 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、551.59 kPa 条件下， 以59%的产率得到6-methyl-6,11-dihydro-5H-indeno[1,2-c]isoquinolin-5-one
  参考文献：
  名称：

  Convenient synthesis of indeno[1,2-c]isoquinolines as constrained forms of 3-arylisoquinolines and docking study of a topoisomerase I inhibitor into DNA–topoisomerase I complex

  摘要：

  11-Hydroxyindeno[1,2-c]isoquinotines 12a-c were prepared as constrained forms of 3-arylisoquinolines through an intramolecular cyclization reaction. Among the synthesized compounds, the 11-butoxy analog 15I displayed potent in vitro cytotoxicity against four different tumor cell lines as well as topoisomerase I inhibitory activity. A FlexX docking study was performed to explain the topoisomerase I activity of 151. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.08.062
• 作为产物：
  描述：

  2-乙烯基苯甲酰氯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 双(三甲基硅烷基)氨基钾 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 38.33h， 生成 11-hydroxy-6-methyl-11H-indeno[1,2-c]isoquinolin-5-one
  参考文献：
  名称：

  Suzuki–Miyaura cross-coupling and ring-closing metathesis: a strategic combination to the synthesis of indeno[1,2-c]isoquinolin-5,11-diones

  摘要：

  A variety of diversely substituted isoindeno[1,2-c]isoquinolin-5,11-diones has been readily assembled through a sequence involving a Suzuki-Miyaura cross-coupling reaction with enol phosphates combined with a ring-closing metathesis (RCM) reaction. Intramolecular carbocationic annulation reaction and ultimate oxidation of a latent hydroxyl functionality completed the synthesis of the target titled compounds. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.113

文献信息

• Convenient synthesis of indeno[1,2-c]isoquinolines as constrained forms of 3-arylisoquinolines and docking study of a topoisomerase I inhibitor into DNA–topoisomerase I complex
  作者：Hue Thi My Van、Quynh Manh Le、Kwang Youl Lee、Eung-Seok Lee、Youngjoo Kwon、Tae Sung Kim、Thanh Nguyen Le、Suh-Hee Lee、Won-Jea Cho

  DOI：10.1016/j.bmcl.2007.08.062

  日期：2007.11

  11-Hydroxyindeno[1,2-c]isoquinotines 12a-c were prepared as constrained forms of 3-arylisoquinolines through an intramolecular cyclization reaction. Among the synthesized compounds, the 11-butoxy analog 15I displayed potent in vitro cytotoxicity against four different tumor cell lines as well as topoisomerase I inhibitory activity. A FlexX docking study was performed to explain the topoisomerase I activity of 151. (c) 2007 Elsevier Ltd. All rights reserved.
• Suzuki–Miyaura cross-coupling and ring-closing metathesis: a strategic combination to the synthesis of indeno[1,2-c]isoquinolin-5,11-diones
  作者：Stéphane Lebrun、Axel Couture、Eric Deniau、Pierre Grandclaudon

  DOI：10.1016/j.tetlet.2011.01.113

  日期：2011.3

  A variety of diversely substituted isoindeno[1,2-c]isoquinolin-5,11-diones has been readily assembled through a sequence involving a Suzuki-Miyaura cross-coupling reaction with enol phosphates combined with a ring-closing metathesis (RCM) reaction. Intramolecular carbocationic annulation reaction and ultimate oxidation of a latent hydroxyl functionality completed the synthesis of the target titled compounds. (c) 2011 Elsevier Ltd. All rights reserved.