2-chloro-1-(4-methoxybenzyl)-1H-benzo[d]imidazole | 388574-61-6

• 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-chloro-1-(4-methoxybenzyl)-1H-benzo[d]imidazole
• 英文别名: 2-chloro-1-[(4-methoxyphenyl)methyl]benzimidazole
• CAS: 388574-61-6
• 化学式: C₁₅H₁₃ClN₂O
• 分子量: 272.734
• InChiKey: OYWPBUVWLRGAPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  463.0±47.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-1-(4-methoxybenzyl)-1H-benzo[d]imidazole 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 10-[(4-methoxyphenyl)methyl]-2H-[1,2,4]triazino[4,3-a]benzimidazole-3,4-dione
  参考文献：
  名称：

  [1,2,4]Triazino[4,3-a]benzimidazole Acetic Acid Derivatives:  A New Class of Selective Aldose Reductase Inhibitors

  摘要：

  Acetic acid derivatives of [1,2,4]triazino[4,3-alpha ]benzimidazole (TBI) were synthesized and tested in vitro and in vivo as a novel class of aldose reductase (ALR2) inhibitors. Compound 3, (10-benzyl[1,2,4]triazino[4,3-alpha ]benzimidazol-3,4(10H)-dion-2-yl)acetic acid, displayed the highest inhibitory activity (IC50 = 0.36 muM) and was found to be effective in preventing cataract development in severely galactosemic rats when administered as an eyedrop solution. All the compounds investigated were selective for ALR2, since none of them inhibited appreciably aldehyde reductase, sorbitol dehydrogenase, or glutathione reductase. The activity of 3 was lowered by inserting various substituents on the pendant phenyl ring, by shifting the acetic acid moiety from the 2 to the 3 position of the TBI nucleus, or by cleaving the TBI system to yield benzimidazolylidenehydrazines as open-chain analogues. A three-dimensional model of human ALR2 was built, taking into account the conformational. changes induced by the binding of inhibitors such as zopolrestat, to simulate the docking of 3 into the enzyme active site. The theoretical binding mode of 3 was fully consistent with the structure-activity relationships in the TBI series and will guide the design of novel ALR2 inhibitors.

  DOI：

  10.1021/jm0109210
• 作为产物：
  描述：

  2-氯苯并咪唑 、 4-甲氧基溴苄 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以32%的产率得到2-chloro-1-(4-methoxybenzyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Host-Directed Inhibitors of Myxoviruses: Synthesis and in Vitro Biochemical Evaluation

  摘要：

  Drugs targeted to viral proteins are highly vulnerable to the development of viral resistance. One little explored approach to the treatment of viral diseases is the development of agents that target host factors required for virus replication. Myxoviruses are predominantly associated with acute disease and, thus, ideally suited for this approach since the necessary treatment time is anticipated to be limited. High-throughput screening previously identified benzimidazole 22407448 with broad antiviral activity against different influenza virus and paramyxovirus strains. Hit to lead chemistry has generated 6p (JMN3-003) with potent antiviral activity against a panel of myxovirus family members exhibiting EC(50) values in the low nanomolar range.

  DOI：

  10.1021/ml200125r

文献信息

• [EN] PYRAZINE COMPOUNDS AS PHOSPHODIESTERASE 10 INHIBITORS<br/>[FR] COMPOSES DE PYRAZINE COMME INHIBITEURS DE PHOSPHODIESTERASE 10
  申请人：AMGEN INC

  公开号：WO2010057121A1

  公开（公告）日：2010-05-20

  Pyrazine compounds, and compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.

  吡嗪化合物、含有它们的组合物以及制备这些化合物的方法。还提供了通过抑制PDE10治疗可治疗的疾病或病症的方法，例如肥胖、非胰岛素依赖型糖尿病、精神分裂症、双相情感障碍、强迫症等。
• PYRIDINE AND PYRIMIDINE DERIVATIVES AS PHOSPHODIESTERASE 10 INHIBITORS
  申请人：Allen Jennifer R.

  公开号：US20100125062A1

  公开（公告）日：2010-05-20

  Pyridine and pyrimidine compounds, and compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.

  吡啶和嘧啶化合物，以及含有它们的组合物，以及制备这些化合物的方法。本文还提供了治疗通过抑制PDE10可治疗的疾病或疾病的方法，如肥胖症、非胰岛素依赖型糖尿病、精神分裂症、躁郁症、强迫症等。
• Pyrazine compounds as phosphodiesterase 10 inhibitors
  申请人：Amgen Inc.

  公开号：US08053438B2

  公开（公告）日：2011-11-08

  Pyrazine compounds, and compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.

  本文提供了吡嗪化合物及含有它们的组合物以及制备这些化合物的方法。此外，本文还提供了治疗PDE10抑制剂可治疗的疾病或疾病的方法，例如肥胖症、非胰岛素依赖性糖尿病、精神分裂症、躁郁症、强迫症等。
• PYRAZINE COMPOUNDS AS PHOSPHODIESTERASE 10 INHIBITORS
  申请人：Allen Jennifer R.

  公开号：US20110160182A1

  公开（公告）日：2011-06-30

  Pyrazine compounds, and compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.

  本发明提供了吡嗪化合物、含有它们的组合物以及制备这些化合物的方法。本发明还提供了治疗通过抑制PDE10可治疗的疾病或疾病的方法，例如肥胖症、非胰岛素依赖性糖尿病、精神分裂症、双相障碍、强迫症等。
• Pyridine and pyrimidine derivatives as phosphodiesterase 10 inhibitors
  申请人：Amgen Inc.

  公开号：US08318718B2

  公开（公告）日：2012-11-27

  Pyridine and pyrimidine compounds, and compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.

  吡啶和嘧啶化合物及含有它们的组合物，并且提供了制备这些化合物的方法。此外，本文还提供了一种治疗可通过抑制PDE10治疗的疾病或疾病的方法，例如肥胖症，非胰岛素依赖性糖尿病，精神分裂症，双相障碍，强迫症等。