2,2'-[1,4-phenylenebis(methyleneoxy-1,4-phenylene)]bis-1H-benzimidazole | 1352120-66-1

• 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: 2,2'-[1,4-phenylenebis(methyleneoxy-1,4-phenylene)]bis-1H-benzimidazole
• 英文别名: 1,4-bis((4-(1H-benzo[d]imidazol-2-yl)phenoxy)methyl)benzene；1,4-bis((4-(1H-benzimidazol-2-yl)phenoxy)methyl)benzene；2-[4-[[4-[[4-(1H-benzimidazol-2-yl)phenoxy]methyl]phenyl]methoxy]phenyl]-1H-benzimidazole
• CAS: 1352120-66-1
• 化学式: C₃₄H₂₆N₄O₂
• 分子量: 522.606
• InChiKey: KXYSAUJQFJDVNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  75.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,4-benzyloxy-bis(4-benzaldehyde) 、 邻苯二胺 在 manganese (II) nitrate tetrahydrate 作用下， 以 乙醇 为溶剂， 反应 0.2h， 以74%的产率得到2,2'-[1,4-phenylenebis(methyleneoxy-1,4-phenylene)]bis-1H-benzimidazole
  参考文献：
  名称：

  Synthesis of 2-arylbenzimidazoles catalyzed by transition metal nitrates

  摘要：

  在催化量的 M(NO3)2·6H2O (M = Mn、Fe、Co、Ni、描述了室温下在乙醇中的Cu)。该实用方法的主要优点是使用容易获得的催化剂、高产率、短反应时间以及反应和后处理简单。

  DOI：

  10.1007/s11164-012-0825-1

文献信息

• Synthesis of novel bis‐ and poly(benzimidazoles) as well as bis‐ and poly(benzothiazoles) as anticancer agents
  作者：Ali M. S. Hebishy、Mohamed S. Abdelfattah、Abdullah Elmorsy、Ahmed H. M. Elwahy

  DOI：10.1002/jhet.3947

  日期：2020.5

  A synthesis of bis‐ and poly(benzimidazoles) as well as bis‐ and poly(benzothiazoles) was attempted using different protocols. The best results were obtained by employing the reaction of the appropriate bis‐ or poly(aldehydes) with o‐phenylenediamine or 2‐aminothiophenol, respectively, in ethanol at reflux in the presence of NaHSO3. The anticancer activities of the synthesized compounds were evaluated

  尝试使用不同的方案合成双和聚苯并咪唑以及双和聚苯并噻唑。通过在NaHSO 3存在下，在乙醇中回流使适当的双醛或多醛分别与邻苯二胺或2-氨基硫酚反应，可获得最佳结果。评估了合成化合物对人乳腺癌细胞系（MCF-7），肝癌细胞系（HepG-2）和上皮结直肠腺癌细胞（CaCO-2）的抗癌活性。已发现Hexakis（苯并噻唑）对HepG-2和MCF-7细胞系的活性最高，IC 50值分别为21.16和13.25μM。
• Bis(oxyphenylene)benzimidazoles: A novel class of anti-Plasmodium falciparum agents
  作者：Annie Mayence、Jean Jacques Vanden Eynde、Marcel Kaiser、Reto Brun、Nigel Yarlett、Tien L. Huang

  DOI：10.1016/j.bmc.2011.10.039

  日期：2011.12

  A small library of 26 2,2'-[alkane-alpha,omega-diylbis(oxyphenylene)] bis-1H-benzimidazoles has been prepared and evaluated against Giardia intestinalis, Entamoeba histolytica, Trypanosoma brucei rhodesiense, Trypanosoma cruzi, Leishmania donovani, and Plasmodium falciparum. Among the tested compounds, eight derivatives (17, 19, 20, 24, 27, 30, 32 and 35) exhibited an anti-Plasmodium falciparum activity characterized by IC50 values in the range of 180-410 nM (0.11-0.21 mu g/mL) and selectivity indexes (IC50 rat skeletal myoblasts L6 cells vs IC50 P. falciparum K1 strain) varying between 92 and more than 450. Two of the eight novel drug leads, namely compounds 19 and 32, were also active against G. intestinalis and L. donovani with selectivity indexes of 122 and > 164 respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of 2-arylbenzimidazoles catalyzed by transition metal nitrates
  作者：Mehdi Kalhor、Akbar Mobinikhaledi、Javad Jamshidi

  DOI：10.1007/s11164-012-0825-1

  日期：2013.9

  A simple and practical procedure for synthesis of 2-arylbenzimidazoles by a one-pot condensation of o-phenylenediamine with aromatic aldehydes in the presence of a catalytic amount of M(NO3)2·6H2O (M = Mn, Fe, Co, Ni, Cu) in ethanol at room temperature is described. Major advantages of this practical procedure are use of a readily available catalyst, high yields, short reaction times, and simplicity of the reaction and workup.

  在催化量的 M(NO3)2·6H2O (M = Mn、Fe、Co、Ni、描述了室温下在乙醇中的Cu)。该实用方法的主要优点是使用容易获得的催化剂、高产率、短反应时间以及反应和后处理简单。