2-(1-bromo-2-naphthyl)-4,7-dimethoxy-1H-benzimidazole | 1187828-52-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-bromo-2-naphthyl)-4,7-dimethoxy-1H-benzimidazole
• 英文别名: 2-(1-bromonaphthalen-2-yl)-4,7-dimethoxy-1H-benzimidazole
• CAS: 1187828-52-9
• 化学式: C₁₉H₁₅BrN₂O₂
• 分子量: 383.244
• InChiKey: FQJBQBSLLHJWAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氰胺 、 2-(1-bromo-2-naphthyl)-4,7-dimethoxy-1H-benzimidazole 在 potassium phosphate 、 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以61%的产率得到
  参考文献：
  名称：

  铜催化的C（sp2）–N偶联和环化，然后氧化，合成2-氨基喹唑啉和2-氨基嘧啶融合杂种支架

  摘要：

  通过初始铜催化的C–N偶联和2‐（2‐溴代芳基）‐和2‐2‐（2-溴乙烯基）‐4,7‐二甲氧基苯并咪唑与氰胺的环化反应，开发了N融合杂化支架的空前合成。结构单元，然后进行氧化。使用这种方法在构建含氨基的多核N融合杂种支架方面将面临更多挑战。

  DOI：

  10.1002/ejoc.202000427
• 作为产物：
  描述：

  2,3-二氨基-1,4-二甲氧基苯 、 1-溴-2-萘甲醛 在 ammonium cerium (IV) nitrate 、 双氧水 作用下， 以 水 为溶剂， 反应 0.17h， 生成 2-(1-bromo-2-naphthyl)-4,7-dimethoxy-1H-benzimidazole
  参考文献：
  名称：

  Synthesis of substituted benzimidazo[2,1-a]isoquinolines and its condensed analogues using Pd(0)-catalyzed cyclization/C–H activation

  摘要：

  An efficient route for the synthesis of benzimidazo[2,1-a]isoquinolines and its condensed analogues has been developed via the palladium-catalyzed cyclization/C-H activation of N-allyl and N-methallyl derivatives of benzimidazoles. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.162

文献信息

• Synthesis and toxicity towards normal and cancer cell lines of benzimidazolequinones containing fused aromatic rings and 2-aromatic ring substituents
  作者：Eoin Moriarty、Miriam Carr、Sarah Bonham、Michael P. Carty、Fawaz Aldabbagh

  DOI：10.1016/j.ejmech.2010.05.025

  日期：2010.9

  A facile 6-exo-trig cyclization of sigma-aromatic radicals has allowed the synthesis of various aromatic ring fused benzimidazoles and benzimidazolequinones. The most highly conjugated naphthyl fused benzimidazolequinone, (5-methyl-5,6-dihydrobenzimidazo[2,1-a]benzo[f]isoquinoline-8,11-dione) showed the highest specificity towards human cervical (HeLa) and prostate (DU145) cancer cell lines with little toxicity towards a human normal (GM00637) cell line at doses of <1 mu M. In contrast, 2-aromatic ring substituted (benzimidazole-4,7-diones) analogues, benzimidazolequinone with a pyridine ring and mitomycin C were more toxic than the highly conjugated naphthyl fused benzimidazolequinone towards the normal cell line. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Synthesis of aryl ring-fused benzimidazolequinones using 6-exo-trig radical cyclizations
  作者：Eoin Moriarty、Fawaz Aldabbagh

  DOI：10.1016/j.tetlet.2009.07.023

  日期：2009.9

  The preparation of alicyclic ring-fused tetracyclic and pentacyclic benzimidazoles containing one and two fused aryl rings, respectively, is achieved conveniently in three steps, including Bu3SnH-mediated 6-exo-trig cyclization of sigma-aryl radicals generated from 1-allyl-2-(omega-bromoaryl)benzimidazoles. Inclusion Of 4,7-dimethoxy substituents on the radical precursors allows access to aryl ring-fused benzimidazolequitiones, a Unique family of potential bioreductive anti-cancer agents. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of substituted benzimidazo[2,1-a]isoquinolines and its condensed analogues using Pd(0)-catalyzed cyclization/C–H activation
  作者：Sukla Nandi、Shubhankar Samanta、Susovan Jana、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2010.07.162

  日期：2010.10

  An efficient route for the synthesis of benzimidazo[2,1-a]isoquinolines and its condensed analogues has been developed via the palladium-catalyzed cyclization/C-H activation of N-allyl and N-methallyl derivatives of benzimidazoles. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of 2-Aminoquinazoline- and 2-Aminopyrimidine-Fused Hybrid Scaffolds by Copper-Catalyzed C(<i>sp</i> ² )-N Coupling and Cyclization Followed by Oxidation
  作者：Jung Pyo Kwak、Pham Duy Quang Dao、Chan Sik Cho

  DOI：10.1002/ejoc.202000427

  日期：2020.6.23

  An unprecedented synthesis of N‐fused hybrid scaffolds has been developed by initial copper‐catalyzed C–N coupling and cyclization of 2‐(2‐bromoaryl)‐ and 2‐(2‐bromovinyl)‐4,7‐dimethoxybenzimidazoles with cyanamide as a building block followed by oxidation. Further challenges on the construction of amino‐group‐containing polynuclear N‐fused hybrid scaffolds using this method are expected.

  通过初始铜催化的C–N偶联和2‐（2‐溴代芳基）‐和2‐2‐（2-溴乙烯基）‐4,7‐二甲氧基苯并咪唑与氰胺的环化反应，开发了N融合杂化支架的空前合成。结构单元，然后进行氧化。使用这种方法在构建含氨基的多核N融合杂种支架方面将面临更多挑战。