1-allyl-2-(1-bromo-2-naphthyl)-4,7-dimethoxy-1H-benzimidazole | 1187828-54-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-allyl-2-(1-bromo-2-naphthyl)-4,7-dimethoxy-1H-benzimidazole
• 英文别名: 2-(1-Bromonaphthalen-2-yl)-4,7-dimethoxy-1-prop-2-enylbenzimidazole
• CAS: 1187828-54-1
• 化学式: C₂₂H₁₉BrN₂O₂
• 分子量: 423.309
• InChiKey: QWTNTPFNHJEZJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-allyl-2-(1-bromo-2-naphthyl)-4,7-dimethoxy-1H-benzimidazole 在 三正丁基氢锡 、 1,1'-偶氮(氰基环己烷) 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以71%的产率得到8,11-dimethoxy-5-methyl-5,6-dihydrobenzimidazo[2,1-a]benzo[f]isoquinoline
  参考文献：
  名称：

  Synthesis of aryl ring-fused benzimidazolequinones using 6-exo-trig radical cyclizations

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.07.023
• 作为产物：
  描述：

  2-(1-bromo-2-naphthyl)-4,7-dimethoxy-1H-benzimidazole 、 3-溴丙烯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以88%的产率得到1-allyl-2-(1-bromo-2-naphthyl)-4,7-dimethoxy-1H-benzimidazole
  参考文献：
  名称：

  Synthesis of aryl ring-fused benzimidazolequinones using 6-exo-trig radical cyclizations

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.07.023

文献信息

• 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 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.