2-(4-phenoxyphenyl)-1H-benzimidazole-5-nitrile | 220955-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(4-phenoxyphenyl)-1H-benzimidazole-5-nitrile
• 英文别名: 2-(4-Phenoxy-phenyl)-1H-benzoimidazole-5-carbonitrile；2-(4-phenoxyphenyl)-3H-benzimidazole-5-carbonitrile
• CAS: 220955-72-6
• 化学式: C₂₀H₁₃N₃O
• 分子量: 311.343
• InChiKey: DJHDCPGWYHIZLY-UHFFFAOYSA-N

物化性质

• 沸点：
  548.4±56.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-phenoxyphenyl)-1H-benzimidazole-5-nitrile 以 盐酸 、 乙醇 、 二氯甲烷 为溶剂， 生成 2-(4-Phenoxy-phenyl)-3H-benzoimidazole-5-carboxamidine
  参考文献：
  名称：

  2-substituted phenyl-benzimidazole antibacterial agents

  摘要：

  本发明涉及化合物的苯并咪唑抗菌化合物的公式 I：如所述，含有这些化合物的药物组合物，以及它们的生产和使用方法。这些化合物在抑制细菌组氨酸蛋白激酶的作用方面是有效的，并且可用作抗感染剂，用于对抗各种细菌生物，包括对其他已知抗生素产生抗性的生物。

  公开号：

  US05942532A1
• 作为产物：
  描述：

  4-苯氧基苯甲醛 、 3,4-二氨基苯甲腈 在 sodium metabisulfite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以21%的产率得到2-(4-phenoxyphenyl)-1H-benzimidazole-5-nitrile
  参考文献：
  名称：

  Checkpoint Kinase Inhibitors:  SAR and Radioprotective Properties of a Series of 2-Arylbenzimidazoles

  摘要：

  The discovery of a series of novel, potent, and highly selective inhibitors of the DNA damage control kinase chk2 is disclosed. Here we report the first SAR study around inhibitors of this kinase. High-throughput screening of purified human chk2 led to the identification of a novel series of 2-arylbenzimidazole inhibitors of the kinase. Optimization was facilitated using homology models of chk2 and docking of inhibitors, leading to the highly potent 2-arylbenzimidazole 2h (IC50 15 nM). Compound 2h is an ATP-competitive inhibitor of chk2 that dose dependently protects human CD4+ and CD8+ T-cells from apoptosis due to ionizing radiation. This work suggests that a selective small molecule inhibitor of chk2 could be a useful adjuvant to radiotherapy, increasing the therapeutic window of such treatment.

  DOI：

  10.1021/jm0495935

文献信息

• US5942532A
  申请人：——

  公开号：US5942532A

  公开（公告）日：1999-08-24
• [EN] 2-SUBSTITUTED PHENYL-BENZIMIDAZOLE ANTIBACTERIAL AGENTS<br/>[FR] AGENTS ANTI-BACTERIENS DE 2-SUBSTITUTE PHENYL-BENZIMIDAZOLE
  申请人：ORTHO-MCNEIL PHARMACEUTICAL, INC.

  公开号：WO1999011627A1

  公开（公告）日：1999-03-11

  (EN) The invention relates to benzimidazole antibacterial compounds of formula (I) as described herein, pharmaceutical compositions containing the compounds, and methods for their production and use. These compounds are effective in inhibiting the action of a bacterial histidine protein kinase and are useful as anti-infective agents against a variety of bacterial organisms, including organisms which are resistant to other known antibiotics.(FR) Cette invention concerne des composés anti-bactériens à base de benzimidazole et répondant à la formule (I) telle que décrite dans le descriptif; des compositions pharmaceutiques renfermant ces composés; et des procédés permettant de les fabriquer et de les utiliser. Ces composés sont des inhibiteurs efficaces de l'action d'une protéine histidine kinase bactérienne et sont utilisés en tant qu'agents anti-infectieux agissant contre une série d'organismes bactériens, y compris les organismes résistant à d'autres antibiotiques connus.
• Checkpoint Kinase Inhibitors:  SAR and Radioprotective Properties of a Series of 2-Arylbenzimidazoles
  作者：Kristen L. Arienti、Anders Brunmark、Frank U. Axe、Kelly McClure、Alice Lee、Jon Blevitt、Danielle K. Neff、Liming Huang、Shelby Crawford、Chennagiri R. Pandit、Lars Karlsson、J. Guy Breitenbucher

  DOI：10.1021/jm0495935

  日期：2005.3.1

  The discovery of a series of novel, potent, and highly selective inhibitors of the DNA damage control kinase chk2 is disclosed. Here we report the first SAR study around inhibitors of this kinase. High-throughput screening of purified human chk2 led to the identification of a novel series of 2-arylbenzimidazole inhibitors of the kinase. Optimization was facilitated using homology models of chk2 and docking of inhibitors, leading to the highly potent 2-arylbenzimidazole 2h (IC50 15 nM). Compound 2h is an ATP-competitive inhibitor of chk2 that dose dependently protects human CD4+ and CD8+ T-cells from apoptosis due to ionizing radiation. This work suggests that a selective small molecule inhibitor of chk2 could be a useful adjuvant to radiotherapy, increasing the therapeutic window of such treatment.
• 2-substituted phenyl-benzimidazole antibacterial agents
  申请人：Ortho Pharmaceutical Corporation

  公开号：US05942532A1

  公开（公告）日：1999-08-24

  The invention relates to benzimidazole antibacterial compounds of the Formula I: ##STR1## as described herein, pharmaceutical compositions containing the compounds, and methods for their production and use. These compounds are effective in inhibiting the action of a bacterial histidine protein kinase and are useful as anti-infective agents against a variety of bacterial organisms, including organisms which are resistant to other known antibiotics.

  本发明涉及化合物的苯并咪唑抗菌化合物的公式 I：如所述，含有这些化合物的药物组合物，以及它们的生产和使用方法。这些化合物在抑制细菌组氨酸蛋白激酶的作用方面是有效的，并且可用作抗感染剂，用于对抗各种细菌生物，包括对其他已知抗生素产生抗性的生物。