benzo[4,5]indolo[2,1-b]quinazoline-8,14-dione | 1394238-48-2

• 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: benzo[4,5]indolo[2,1-b]quinazoline-8,14-dione
• 英文别名: benzo[c]tryptanthrin；2,10-diazapentacyclo[11.8.0.02,11.04,9.014,19]henicosa-1(13),4,6,8,10,14,16,18,20-nonaene-3,12-dione
• CAS: 1394238-48-2
• 化学式: C₁₉H₁₀N₂O₂
• 分子量: 298.301
• InChiKey: URYGDNBRLLLDEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,5-苯并靛红 、 邻氨基苯甲酸 在 吡啶 、 氯化亚砜 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以57%的产率得到benzo[4,5]indolo[2,1-b]quinazoline-8,14-dione
  参考文献：
  名称：

  Synthesis of benzo-annulated tryptanthrins and their biological properties

  摘要：

  A series of benzo-annulated derivatives of tryptanthrin were prepared and their optical and redox properties were studied. Tryptanthrin and its benzo-annulated derivatives showed selective inhibitory activity on topo I with an increase of activity on topo II by benzo-annulation on quinazolin-4(3H)-one moiety. Although the benzo-annulation on quinazolin-4(3H)-one ring did not affect significantly on the inhibitory activities against topo I and II, the benzoannulation on indolin-3-one ring affected the inhibitory activity very much especially by linear annulation. Cytotoxicities were not significantly changed upon benzoannulation, which were not directly related either to the inhibitory activities against topo I and II or to the reduction potentials. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.034

文献信息

• Aryne Insertion Reactions Leading to Bioactive Fused Quinazolinones: Diastereoselective Total Synthesis of Cruciferane
  作者：Sagar D. Vaidya、Narshinha P. Argade

  DOI：10.1021/ol4018062

  日期：2013.8.2

  Insertion reactions of an in situ generated arynes to a variety of suitably substituted 1,3-quinazolin-4-ones have been demonstrated for a new efficient one-step approach to a diverse range of fused quinazolinone architectures. The present protocol has been effectively utilized to accomplish the concise total synthesis of recently isolated bioactive natural products tryptanthrin, phaitanthrins A-C, and cruciferane.
• Synthesis of benzo-annulated tryptanthrins and their biological properties
  作者：Jing Lu Liang、So-Eun Park、Youngjoo Kwon、Yurngdong Jahng

  DOI：10.1016/j.bmc.2012.06.034

  日期：2012.8

  A series of benzo-annulated derivatives of tryptanthrin were prepared and their optical and redox properties were studied. Tryptanthrin and its benzo-annulated derivatives showed selective inhibitory activity on topo I with an increase of activity on topo II by benzo-annulation on quinazolin-4(3H)-one moiety. Although the benzo-annulation on quinazolin-4(3H)-one ring did not affect significantly on the inhibitory activities against topo I and II, the benzoannulation on indolin-3-one ring affected the inhibitory activity very much especially by linear annulation. Cytotoxicities were not significantly changed upon benzoannulation, which were not directly related either to the inhibitory activities against topo I and II or to the reduction potentials. (C) 2012 Elsevier Ltd. All rights reserved.