19-[(4-Methoxyphenyl)methyl]-15-methyl-8-oxa-19-azatetracyclo[9.8.0.02,7.012,17]nonadeca-1(11),2,4,6,12(17),13,15-heptaen-18-one | 1160642-72-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 19-[(4-Methoxyphenyl)methyl]-15-methyl-8-oxa-19-azatetracyclo[9.8.0.02,7.012,17]nonadeca-1(11),2,4,6,12(17),13,15-heptaen-18-one
• CAS: 1160642-72-7
• 化学式: C₂₆H₂₃NO₃
• 分子量: 397.474
• InChiKey: KTZWRGIZZAGSBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-Bromo-3-(2-ethenoxyphenyl)-2-[(4-methoxyphenyl)methyl]-7-methylisoquinolin-1-one 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 生成 19-[(4-Methoxyphenyl)methyl]-15-methyl-8-oxa-19-azatetracyclo[9.8.0.02,7.012,17]nonadeca-1(11),2,4,6,12(17),13,15-heptaen-18-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.