4-[(2-Chlorobenzimidazol-1-yl)methyl]aniline | 1219829-22-7

• 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: 4-[(2-Chlorobenzimidazol-1-yl)methyl]aniline
• CAS: 1219829-22-7
• 化学式: C₁₄H₁₂ClN₃
• 分子量: 257.722
• InChiKey: LGGGDCXDBUFOGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 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：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[(2-Chlorobenzimidazol-1-yl)methyl]aniline 在 一水合肼 作用下， 反应 5.0h， 生成 4-[(2-Hydrazinylbenzimidazol-1-yl)methyl]aniline
  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 在 palladium 10% on activated carbon 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 4-[(2-Chlorobenzimidazol-1-yl)methyl]aniline
  参考文献：
  名称：

  含有苯并咪唑/吡唑啉酮/1,3,4-恶二唑基序的吡咯杂芳唑的合成和细胞毒性评价。

  摘要：

  合成了含有苯并咪唑/吡唑酮/1,3,4-恶二唑的偶氮甲碱连接的吡咯二杂芳唑，收率令人满意。其结构经IR、1H-NMR、13C-NMR和元素分析证实。对一组乳腺癌细胞系（MDA-AB-231、BT-474 和 Ishikawa 细胞）的体外细胞毒活性评估表明，吡咯-苯并咪唑杂合体比吡唑啉酮和 1,3,4-恶二唑更有效所有细胞系中的杂种。化合物 (9) 对 BT-474 细胞系表现出良好的细胞毒性，IC50 值为 7.7 µM。

  DOI：

  10.1002/jhet.2501

文献信息

• Synthesis and Cytotoxic Evaluation of Pyrrole Hetarylazoles Containing Benzimidazole/Pyrazolone/1,3,4-Oxadiazole Motifs
  作者：Bereket Mochona、Timothy Jackson、DeCoria McCauley、Elizabeth Mazzio、Kinfe K. Redda

  DOI：10.1002/jhet.2501

  日期：2016.11

  Azomethine linked pyrrole bishetarylazoles containing benzimidazole/pyrazolone/1,3,4-oxadiazole were synthesized in satisfactory yields. Their structures were confirmed by IR, 1H-NMR, 13C-NMR and elemental analysis. Evaluation for the cytotoxic activities In vitro against a panel of breast cancer cell lines (MDA-AB-231, BT-474 and Ishikawa cells) revealed that the pyrrole-benzimidazole hybrids are

  合成了含有苯并咪唑/吡唑酮/1,3,4-恶二唑的偶氮甲碱连接的吡咯二杂芳唑，收率令人满意。其结构经IR、1H-NMR、13C-NMR和元素分析证实。对一组乳腺癌细胞系（MDA-AB-231、BT-474 和 Ishikawa 细胞）的体外细胞毒活性评估表明，吡咯-苯并咪唑杂合体比吡唑啉酮和 1,3,4-恶二唑更有效所有细胞系中的杂种。化合物 (9) 对 BT-474 细胞系表现出良好的细胞毒性，IC50 值为 7.7 µM。
• 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.