8-benzyl-7-phenyl-6,8-dihydro-5H-pyrrolo[3,4-h]quinazoline | 1189364-04-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 8-benzyl-7-phenyl-6,8-dihydro-5H-pyrrolo[3,4-h]quinazoline
• 英文别名: 8-Benzyl-7-phenyl-6,4-h]quinazoline；8-benzyl-7-phenyl-5,6-dihydropyrrolo[3,4-h]quinazoline
• CAS: 1189364-04-2
• 化学式: C₂₃H₁₉N₃
• 分子量: 337.424
• InChiKey: YXJFOCJJDOTEQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-oxo-1-phenyl-4,5,6,7-tetrahydroisoindole 在 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 formamide 、 mineral oil 为溶剂， 反应 26.0h， 生成 8-benzyl-7-phenyl-6,8-dihydro-5H-pyrrolo[3,4-h]quinazoline
  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

文献信息

• Synthesis of the new ring system 6,8-dihydro-5H-pyrrolo[3,4-h]quinazoline
  作者：Paola Barraja、Virginia Spanò、Patrizia Diana、Anna Carbone、Girolamo Cirrincione

  DOI：10.1016/j.tetlet.2009.07.045

  日期：2009.9

  A convenient synthesis of the pyrrolo[3,4-h]quinazoline ring system is reported. Our synthetic approach consisted of the annelation of a pyrimidine ring to an isoindole moiety using tetrahydroisoindole-4-ones as building blocks. The antiproliferative activity of the new compounds was investigated and one of them showed antitumor activity against all the 59 tested cell lines at micromolar concentrations

  报道了吡咯并[3，4- h ]喹唑啉环系统的方便合成。我们的合成方法包括使用四氢异吲哚-4-酮作为构建基，使嘧啶环与异吲哚部分成环。研究了新化合物的抗增殖活性，其中一种在微摩尔浓度（1.46-18.4μM）下显示了对所有59种测试细胞系的抗肿瘤活性。
• Synthesis of a new class of pyrrolo[3,4-h]quinazolines with antimitotic activity
  作者：Virginia Spanò、Alessandra Montalbano、Anna Carbone、Barbara Parrino、Patrizia Diana、Girolamo Cirrincione、Ignazio Castagliuolo、Paola Brun、Olaf-Georg Issinger、Silvia Tisi、Irina Primac、Daniela Vedaldi、Alessia Salvador、Paola Barraja

  DOI：10.1016/j.ejmech.2013.10.014

  日期：2014.3

  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.