2-chloro-1-(4-chloro-2-fluorobenzyl)-1H-benzo[d]imidazole | 1219829-26-1

• 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-chloro-2-fluorobenzyl)-1H-benzo[d]imidazole
• 英文别名: 2-Chloro-1-[(4-chloro-2-fluorophenyl)methyl]benzimidazole
• CAS: 1219829-26-1
• 化学式: C₁₄H₉Cl₂FN₂
• 分子量: 295.143
• InChiKey: LOQXFTHDLRWWKD-UHFFFAOYSA-N

物化性质

• 沸点：
  448.4±55.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.8
• 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-chloro-2-fluorobenzyl)-1H-benzo[d]imidazole 在 一水合肼 作用下， 反应 5.0h， 生成 [1-[(4-Chloro-2-fluorophenyl)methyl]benzimidazol-2-yl]hydrazine
  参考文献：
  名称：

  RETRACTED: Synthesis and biological evaluation of [1,2,4]triazino[4,3-a] benzimidazole acetic acid derivatives as selective aldose reductase inhibitors

  摘要：

  The acetic acid derivatives of [1,2,4]triazino[4,3-a]benzimidazole (TBI) were synthesized and tested in vitro and in vivo as selective aldose reductase (ALR2) inhibitors. Compound PS11 showed highest inhibitory activity (IC50) 0.32 mu M 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. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.11.031
• 作为产物：
  描述：

  2-氯苯并咪唑 、 4-氯-2-氟苄溴 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 13.0h， 生成 2-chloro-1-(4-chloro-2-fluorobenzyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Design, synthesis and characterization of novel N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors leading to the identification of the selective compound, AC1903

  摘要：

  The transient receptor potential cation channel 5 (TRPC5) has been previously shown to affect podocyte survival in the kidney. As such, inhibitors of TRPC5 are interesting candidates for the treatment of chronic kidney disease (CKD). Herein, we report the synthesis and biological characterization of a series of N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors. Work reported here evaluates the benzimidazole scaffold and substituents resulting in the discovery of AC1903, a TRPC5 inhibitor that is active in multiple animal models of CKD.

  DOI：

  10.1016/j.bmcl.2018.12.007

文献信息

• Design, synthesis and characterization of novel N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors leading to the identification of the selective compound, AC1903
  作者：Swagat H. Sharma、Juan Lorenzo Pablo、Monica Suarez Montesinos、Anna Greka、Corey R. Hopkins

  DOI：10.1016/j.bmcl.2018.12.007

  日期：2019.1

  The transient receptor potential cation channel 5 (TRPC5) has been previously shown to affect podocyte survival in the kidney. As such, inhibitors of TRPC5 are interesting candidates for the treatment of chronic kidney disease (CKD). Herein, we report the synthesis and biological characterization of a series of N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors. Work reported here evaluates the benzimidazole scaffold and substituents resulting in the discovery of AC1903, a TRPC5 inhibitor that is active in multiple animal models of CKD.
• RETRACTED: Synthesis and biological evaluation of [1,2,4]triazino[4,3-a] benzimidazole acetic acid derivatives as selective aldose reductase inhibitors
  作者：Prasanta Kumar Sahoo、Pritishova Behera

  DOI：10.1016/j.ejmech.2009.11.031

  日期：2010.3

  The acetic acid derivatives of [1,2,4]triazino[4,3-a]benzimidazole (TBI) were synthesized and tested in vitro and in vivo as selective aldose reductase (ALR2) inhibitors. Compound PS11 showed highest inhibitory activity (IC50) 0.32 mu M 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. (C) 2009 Elsevier Masson SAS. All rights reserved.