2,2'-[1,6-hexanediylbis(oxy-1,3-phenylene)]bis-1H-benzimidazole | 1352120-56-9

• 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'-[1,6-hexanediylbis(oxy-1,3-phenylene)]bis-1H-benzimidazole
• 英文别名: 2-[3-[6-[3-(1H-benzimidazol-2-yl)phenoxy]hexoxy]phenyl]-1H-benzimidazole
• CAS: 1352120-56-9
• 化学式: C₃₂H₃₀N₄O₂
• 分子量: 502.616
• InChiKey: CZPUEKUJKZRZQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  3,3-(1,6-己烷二氧基)双苯甲醛 、 邻苯二胺 在 吡啶 、 氯化亚砜 、 sodium hydroxide 作用下， 以 二氯甲烷 、 乙醇 为溶剂， 反应 0.17h， 以40%的产率得到2,2'-[1,6-hexanediylbis(oxy-1,3-phenylene)]bis-1H-benzimidazole
  参考文献：
  名称：

  Bis(oxyphenylene)benzimidazoles: A novel class of anti-Plasmodium falciparum agents

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2011.10.039

文献信息

• 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.