3-[2-(Methoxymethoxy)phenyl]-2,6-dimethylisoquinolin-1-one | 1160642-80-7

• 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-(Methoxymethoxy)phenyl]-2,6-dimethylisoquinolin-1-one
• CAS: 1160642-80-7
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: SMHCIUZRZCEGQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[2-(Methoxymethoxy)phenyl]-2,6-dimethylisoquinolin-1-one 在 N-溴代丁二酰亚胺(NBS) 、 1,1'-偶氮(氰基环己烷) 作用下， 以 四氯化碳 为溶剂， 生成 4-Bromo-3-[2-(methoxymethoxy)phenyl]-2,6-dimethylisoquinolin-1-one
  参考文献：
  名称：

  Molecular design, synthesis and docking study of benz[b]oxepines and 12-oxobenzo[c]phenanthridinones as topoisomerase 1 inhibitors

  摘要：

  Benz[b]oxepines 4a-g and 12-oxobenzo[c]phenanthridines 5a-d were designed and synthesized as constrained forms of 3-arylisoquinolines through an intramolecular radical cyclization reaction. Radical cyclization of O-vinyl compounds preferentially led to the 7-endo-trig cyclization pathway to the benz[b] oxepines and 12-oxobenzo[c]phenanthridines through 6-exo-trig path as minor products. Among the synthesized compounds, benz[b]oxepine derivative 4e exhibited potent in vitro cytotoxicity against three different tumor cell lines, as well as topoisomerase 1 inhibitory activity. A Surflex-Dock docking study was performed to clarify the topoisomerase 1 activity of 4e. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.058
• 作为产物：
  描述：

  3-[2-(methoxymethoxy)phenyl]-6-methyl-2H-isoquinolin-1-one 、 碘甲烷 在 sodium hydride 作用下， 生成 3-[2-(Methoxymethoxy)phenyl]-2,6-dimethylisoquinolin-1-one
  参考文献：
  名称：

  Molecular design, synthesis and docking study of benz[b]oxepines and 12-oxobenzo[c]phenanthridinones as topoisomerase 1 inhibitors

  摘要：

  Benz[b]oxepines 4a-g and 12-oxobenzo[c]phenanthridines 5a-d were designed and synthesized as constrained forms of 3-arylisoquinolines through an intramolecular radical cyclization reaction. Radical cyclization of O-vinyl compounds preferentially led to the 7-endo-trig cyclization pathway to the benz[b] oxepines and 12-oxobenzo[c]phenanthridines through 6-exo-trig path as minor products. Among the synthesized compounds, benz[b]oxepine derivative 4e exhibited potent in vitro cytotoxicity against three different tumor cell lines, as well as topoisomerase 1 inhibitory activity. A Surflex-Dock docking study was performed to clarify the topoisomerase 1 activity of 4e. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.058

文献信息

• Molecular design, synthesis and docking study of benz[b]oxepines and 12-oxobenzo[c]phenanthridinones as topoisomerase 1 inhibitors
  作者：Suh-Hee Lee、Hue Thi My Van、Su Hui Yang、Kyung-Tae Lee、Youngjoo Kwon、Won-Jea Cho

  DOI：10.1016/j.bmcl.2009.03.058

  日期：2009.5

  Benz[b]oxepines 4a-g and 12-oxobenzo[c]phenanthridines 5a-d were designed and synthesized as constrained forms of 3-arylisoquinolines through an intramolecular radical cyclization reaction. Radical cyclization of O-vinyl compounds preferentially led to the 7-endo-trig cyclization pathway to the benz[b] oxepines and 12-oxobenzo[c]phenanthridines through 6-exo-trig path as minor products. Among the synthesized compounds, benz[b]oxepine derivative 4e exhibited potent in vitro cytotoxicity against three different tumor cell lines, as well as topoisomerase 1 inhibitory activity. A Surflex-Dock docking study was performed to clarify the topoisomerase 1 activity of 4e. (c) 2009 Elsevier Ltd. All rights reserved.