14-benzyl-8,13,13b,14-tetrahydroindolo[2′,3′:3,4]pyrido[2,1-b]-quinazolin-5(7H)-one | 1316852-07-9

• 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: 14-benzyl-8,13,13b,14-tetrahydroindolo[2′,3′:3,4]pyrido[2,1-b]-quinazolin-5(7H)-one
• 英文别名: 21-Benzyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15,17,19-heptaen-14-one；21-benzyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15,17,19-heptaen-14-one
• CAS: 1316852-07-9
• 化学式: C₂₅H₂₁N₃O
• 分子量: 379.461
• InChiKey: LNLLCWRSCBBSTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  39.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  14-benzyl-8,13,13b,14-tetrahydroindolo[2′,3′:3,4]pyrido[2,1-b]-quinazolin-5(7H)-one 在 potassium tert-butylate 、 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以58%的产率得到14-benzyl-1,2-dihydroquinolino[2',3':3,4]pyrrolo[2,1-b]quinazoline-5,8(13H)-dione
  参考文献：
  名称：

  Intramolecular N-aza-amidoalkylation in association with Witkop–Winterfeldt oxidation as the key step to synthesize Luotonin-A analogues

  摘要：

  An expedient four-step approach for the synthesis of a short library of original analogues of the Topo-I Luotonin-A inhibitor, substituted at their C-8- and N-15-positions, was investigated. This consists of Rutaecarpines formation, their Witkop-Winterfeldt oxidation followed ultimately with functional adjustment of the pyrroloquinolone intermediates. In the first step of these investigations. Rutaecarpines including the Topo-I poison Evodiamine were obtained via the new tandem N-acylation/aza-amidoalkylation using a nitrogen atom as an internal nucleophile with or without association with a decarboxylation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.120
• 作为产物：
  描述：

  靛红酸酐 在 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 14-benzyl-8,13,13b,14-tetrahydroindolo[2′,3′:3,4]pyrido[2,1-b]-quinazolin-5(7H)-one
  参考文献：
  名称：

  Intramolecular N-aza-amidoalkylation in association with Witkop–Winterfeldt oxidation as the key step to synthesize Luotonin-A analogues

  摘要：

  An expedient four-step approach for the synthesis of a short library of original analogues of the Topo-I Luotonin-A inhibitor, substituted at their C-8- and N-15-positions, was investigated. This consists of Rutaecarpines formation, their Witkop-Winterfeldt oxidation followed ultimately with functional adjustment of the pyrroloquinolone intermediates. In the first step of these investigations. Rutaecarpines including the Topo-I poison Evodiamine were obtained via the new tandem N-acylation/aza-amidoalkylation using a nitrogen atom as an internal nucleophile with or without association with a decarboxylation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.120

文献信息

• One-Pot Total Synthesis of Evodiamine and Its Analogues through a Continuous Biscyclization Reaction
  作者：Zi-Xuan Wang、Jia-Chen Xiang、Miao Wang、Jin-Tian Ma、Yan-Dong Wu、An-Xin Wu

  DOI：10.1021/acs.orglett.8b02667

  日期：2018.10.19

  The one-pot total synthesis of evodiamine and its analogues is achieved using a three-component reaction. Through continuous biscyclization, various readily available substrates with good functional group tolerance were easily incorporated into biologically active quinazolinocarboline backbones. The use of triethoxymethane as a cosolvent was crucial for this quick and straightforward transformation

  使用三组分反应可实现一锅法合成乙二胺及其类似物。通过连续的双环化，容易将具有良好官能团耐受性的各种容易获得的底物掺入具有生物活性的喹唑啉代咔啉主链中。三乙氧基甲烷作为助溶剂的使用对于这种快速而直接的转化至关重要。
• Discovery of evodiamine derivatives as potential lead antifungal agents for the treatment of superficial fungal infections
  作者：Yan Liang、Honghua Zhang、Xi Zhang、Ying Peng、Jiedan Deng、Yuqing Wang、Ranhui Li、Linyi Liu、Zhen Wang

  DOI：10.1016/j.bioorg.2022.105981

  日期：2022.10
• N(14)-substituted evodiamine derivatives as dual topoisomerase 1/tubulin-Inhibiting anti-gastrointestinal tumor agents
  作者：Jiedan Deng、Lin Long、Xue Peng、Weifan Jiang、Ying Peng、Xi Zhang、Yuting Zhao、Ying Tian、Zhen Wang、Linsheng Zhuo

  DOI：10.1016/j.ejmech.2023.115366

  日期：2023.7
• Intramolecular N-aza-amidoalkylation in association with Witkop–Winterfeldt oxidation as the key step to synthesize Luotonin-A analogues
  作者：Frédéric Pin、Sébastien Comesse、Adam Daïch

  DOI：10.1016/j.tet.2011.05.120

  日期：2011.8

  An expedient four-step approach for the synthesis of a short library of original analogues of the Topo-I Luotonin-A inhibitor, substituted at their C-8- and N-15-positions, was investigated. This consists of Rutaecarpines formation, their Witkop-Winterfeldt oxidation followed ultimately with functional adjustment of the pyrroloquinolone intermediates. In the first step of these investigations. Rutaecarpines including the Topo-I poison Evodiamine were obtained via the new tandem N-acylation/aza-amidoalkylation using a nitrogen atom as an internal nucleophile with or without association with a decarboxylation. (C) 2011 Elsevier Ltd. All rights reserved.