2-[4-Bromo-2-[(4-methoxyphenyl)methyl]-6-methyl-1-oxoisoquinolin-3-yl]benzaldehyde | 946075-40-7

• 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: 2-[4-Bromo-2-[(4-methoxyphenyl)methyl]-6-methyl-1-oxoisoquinolin-3-yl]benzaldehyde
• CAS: 946075-40-7
• 化学式: C₂₅H₂₀BrNO₃
• 分子量: 462.343
• InChiKey: HONGTSLUFQANEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[4-Bromo-2-[(4-methoxyphenyl)methyl]-6-methyl-1-oxoisoquinolin-3-yl]benzaldehyde 在 正丁基锂 、 三正丁基氢锡 、 1,1'-偶氮(氰基环己烷) 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 6-(4-methoxybenzyl)-2,11-dimethyl-6,11-dihydro-5H-indeno[1,2-c]isoquinolin-5-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
• 作为产物：
  描述：

  N,2,4-三甲基苯甲酰胺 在 N-溴代丁二酰亚胺(NBS) 、 重铬酸吡啶 、 正丁基锂 、 水 、 potassium carbonate 、 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 2-[4-Bromo-2-[(4-methoxyphenyl)methyl]-6-methyl-1-oxoisoquinolin-3-yl]benzaldehyde
  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

• 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.