8-methyl-N-phenyl-6,8-dihydro-5H-pyrrolo[3,4-h]quinazolin-2-amine | 1575821-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 8-methyl-N-phenyl-6,8-dihydro-5H-pyrrolo[3,4-h]quinazolin-2-amine
• 英文别名: 8-methyl-N-phenyl-6,4-h]quinazolin-2-amine；8-methyl-N-phenyl-5,6-dihydropyrrolo[3,4-h]quinazolin-2-amine
• CAS: 1575821-82-7
• 化学式: C₁₇H₁₆N₄
• 分子量: 276.341
• InChiKey: JGTDVCOCIPMEDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(hydroxymethylene)-2-methyl-2,5,6,7-tetrahydro-4H-isoindol-4-one 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.0h， 生成 8-methyl-N-phenyl-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

文献信息

• 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.