3-[2-(4-methoxybenzyloxymethyl)phenyl]-2H-isoquinolin-1-one | 325166-90-3

• 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-methoxybenzyloxymethyl)phenyl]-2H-isoquinolin-1-one
• 英文别名: 3-[2-[(4-methoxyphenyl)methoxymethyl]phenyl]-2H-isoquinolin-1-one
• CAS: 325166-90-3
• 化学式: C₂₄H₂₁NO₃
• 分子量: 371.436
• InChiKey: SDCVJQIYGYONFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[2-(4-methoxybenzyloxymethyl)phenyl]-2H-isoquinolin-1-one 在 N-溴代丁二酰亚胺(NBS) 、 重铬酸吡啶 、 正丁基锂 、 水 、 sodium hydride 、 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：

  2-(p-methoxybenzyloxymethyl)benzonitrile 、 N,N-二乙基-2-甲基苯甲酰胺 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以44%的产率得到3-[2-(4-methoxybenzyloxymethyl)phenyl]-2H-isoquinolin-1-one
  参考文献：
  名称：

  Total synthesis of 8-oxypseudopalmatine and 8-oxypseudoberberine via ring-closing metathesis

  摘要：

  Concise synthesis of 8-oxypseudopalmatine and 8-oxypseudoberberine has been achieved using ruthenium-catalyzed ring-closing metathesis (RCM) as the key step, in which the RCM substrates, 3-arylisoquinolinones, were prepared by lithiated cycloaddition reaction with o-toluamides and benzonitriles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.027

文献信息

• Structural modification of 3-arylisoquinolines to isoindolo[2,1-b]isoquinolinones for the development of novel topoisomerase 1 inhibitors with molecular docking study
  作者：Hue Thi My Van、Won-Jea Cho

  DOI：10.1016/j.bmcl.2009.03.042

  日期：2009.5

  Isoindolo[2,1-b]isoquinolinones 9a-i were designed and synthesized as constrained forms of 3-arylisoquinolines through an intramolecular cyclization reaction. Among the synthesized compounds, 9d exhibited potent topoisomerase 1 inhibitory activity with cytotoxicities against three different tumor cell lines. A Surflex-dock docking study was performed to clarify the topoisomerase 1 inhibitory activity of 9d. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.
• Total synthesis of 8-oxypseudopalmatine and 8-oxypseudoberberine via ring-closing metathesis
  作者：Hue Thi My Van、Su Hui Yang、Daulat Bikram Khadka、Yong-Chul Kim、Won-Jea Cho

  DOI：10.1016/j.tet.2009.10.027

  日期：2009.12

  Concise synthesis of 8-oxypseudopalmatine and 8-oxypseudoberberine has been achieved using ruthenium-catalyzed ring-closing metathesis (RCM) as the key step, in which the RCM substrates, 3-arylisoquinolinones, were prepared by lithiated cycloaddition reaction with o-toluamides and benzonitriles. (C) 2009 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.