5-[(diethylamino)methylidene]-2-(4-methoxybenzyl)-1-phenyl-2,5,6,7-tetrahydro-4H-isoindol-4-one | 1575822-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-[(diethylamino)methylidene]-2-(4-methoxybenzyl)-1-phenyl-2,5,6,7-tetrahydro-4H-isoindol-4-one
• CAS: 1575822-00-2
• 化学式: C₂₇H₃₀N₂O₂
• 分子量: 414.547
• InChiKey: OEIGVDXQHYRDOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  34.47
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  苯基胍 、 5-[(diethylamino)methylidene]-2-(4-methoxybenzyl)-1-phenyl-2,5,6,7-tetrahydro-4H-isoindol-4-one 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以65%的产率得到8-(4-methoxybenzyl)-N,7-diphenyl-6,8-dihydro-5H-pyrrolo[3,4-h]quinazolin-2-amine
  参考文献：
  名称：

  Synthesis of a new class of pyrrolo[3,4-h]quinazolines with antimitotic activity

  摘要：

  A new series of pyrrolo[3,4-h]quinazolines was conveniently prepared with a broad substitution pattern. A large number of derivatives was obtained and the cellular cytotoxicity was evaluated in vitro against 5 different human tumor cell lines with GI(50) values reaching the low micromolar level (1.3-19.8 mu M). These compounds were able to induce cell death mainly by apoptosis through a mitochondrial dependent pathway. Selected compounds showed antimitotic activity and a reduction of tubulin polymerization in a concentration-dependent manner. Moreover, they showed anti-angiogenic properties since reduced in vitro endothelial cell migration and disrupted HUVEC capillary-like tube network in Matrigel. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.014
• 作为产物：
  描述：

  4-甲氧基氯苄 在 potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 54.0h， 生成 5-[(diethylamino)methylidene]-2-(4-methoxybenzyl)-1-phenyl-2,5,6,7-tetrahydro-4H-isoindol-4-one
  参考文献：
  名称：

  Synthesis of a new class of pyrrolo[3,4-h]quinazolines with antimitotic activity

  摘要：

  A new series of pyrrolo[3,4-h]quinazolines was conveniently prepared with a broad substitution pattern. A large number of derivatives was obtained and the cellular cytotoxicity was evaluated in vitro against 5 different human tumor cell lines with GI(50) values reaching the low micromolar level (1.3-19.8 mu M). These compounds were able to induce cell death mainly by apoptosis through a mitochondrial dependent pathway. Selected compounds showed antimitotic activity and a reduction of tubulin polymerization in a concentration-dependent manner. Moreover, they showed anti-angiogenic properties since reduced in vitro endothelial cell migration and disrupted HUVEC capillary-like tube network in Matrigel. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.014