3-[2-(4-Methoxy-benzyloxymethyl)-phenyl]-2-methyl-2H-isoquinolin-1-one | 325166-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-[2-(4-Methoxy-benzyloxymethyl)-phenyl]-2-methyl-2H-isoquinolin-1-one
• CAS: 325166-93-6
• 化学式: C₂₅H₂₃NO₃
• 分子量: 385.463
• InChiKey: MQKOYQMQTMGVSY-UHFFFAOYSA-N

物化性质

• 沸点：
  571.1±50.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  40.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-[2-(4-Methoxy-benzyloxymethyl)-phenyl]-2-methyl-2H-isoquinolin-1-one 在 N-溴代丁二酰亚胺(NBS) 、 重铬酸吡啶 、 正丁基锂 、 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 1,1'-偶氮(氰基环己烷) 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 为溶剂， 生成 4-bromo-2-methyl-3-(2-vinylphenyl)-1(2H)-isoquinolinone
  参考文献：
  名称：

  Design, docking, and synthesis of novel indeno[1,2-c]isoquinolines for the development of antitumor agents as topoisomerase I inhibitors

  摘要：

  An intramolecular radical cyclization reaction of 4-bromo-3-arylisoquinolines 11a-c allowed the efficient synthesis of 11-methylindenoisoquinolines 2a-c. 5-(2-Aminoethylainino)indeno[1,2-c]isoquinolin-11-one 4 was also prepared in the convenient manner. The synthesized compounds were tested in vitro for cytotoxicity and DNA-topoisomerase 1 (top 1) inhibitory activity. The dramatic enhancement of top 1 inhibitory activity of 4 was explained by a docking study using the FlexX program. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.064
• 作为产物：
  描述：

  N-甲基邻甲苯酰胺 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 3-[2-(4-Methoxy-benzyloxymethyl)-phenyl]-2-methyl-2H-isoquinolin-1-one
  参考文献：
  名称：

  Design, docking, and synthesis of novel indeno[1,2-c]isoquinolines for the development of antitumor agents as topoisomerase I inhibitors

  摘要：

  An intramolecular radical cyclization reaction of 4-bromo-3-arylisoquinolines 11a-c allowed the efficient synthesis of 11-methylindenoisoquinolines 2a-c. 5-(2-Aminoethylainino)indeno[1,2-c]isoquinolin-11-one 4 was also prepared in the convenient manner. The synthesized compounds were tested in vitro for cytotoxicity and DNA-topoisomerase 1 (top 1) inhibitory activity. The dramatic enhancement of top 1 inhibitory activity of 4 was explained by a docking study using the FlexX program. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.064

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.
• Design, docking, and synthesis of novel indeno[1,2-c]isoquinolines for the development of antitumor agents as topoisomerase I inhibitors
  作者：Won-Jea Cho、Quynh Manh Le、Hue Thi My Van、Kwang Youl Lee、Bok Yun Kang、Eung-Seok Lee、Sang Kook Lee、Youngjoo Kwon

  DOI：10.1016/j.bmcl.2007.04.064

  日期：2007.7

  An intramolecular radical cyclization reaction of 4-bromo-3-arylisoquinolines 11a-c allowed the efficient synthesis of 11-methylindenoisoquinolines 2a-c. 5-(2-Aminoethylainino)indeno[1,2-c]isoquinolin-11-one 4 was also prepared in the convenient manner. The synthesized compounds were tested in vitro for cytotoxicity and DNA-topoisomerase 1 (top 1) inhibitory activity. The dramatic enhancement of top 1 inhibitory activity of 4 was explained by a docking study using the FlexX program. (c) 2007 Elsevier Ltd. All rights reserved.