ethyl 5-(hydroxymethylidene)-3-methyl-2-(4-methylbenzyl)-4-oxo-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate | 1575822-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 5-(hydroxymethylidene)-3-methyl-2-(4-methylbenzyl)-4-oxo-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate
• CAS: 1575822-06-8
• 化学式: C₂₁H₂₃NO₄
• 分子量: 353.418
• InChiKey: PVACATGSNBMWPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.53
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-(hydroxymethylidene)-3-methyl-2-(4-methylbenzyl)-4-oxo-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate 、 尿素 以 乙醇 为溶剂， 反应 24.0h， 以70%的产率得到ethyl 2-hydroxy-9-methyl-8-(4-methylbenzyl)-6,8-dihydro-5H-pyrrolo[3,4-h]quinazoline-7-carboxylate
  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：

  ethyl 3-methyl-2-(p-methylbenzyl)-4-oxo-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate 、 甲酸乙酯 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 27.0h， 以60%的产率得到ethyl 5-(hydroxymethylidene)-3-methyl-2-(4-methylbenzyl)-4-oxo-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate
  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