2,2'-diphenyl-5,5'-bisbenzimidazolyl ether | 73672-91-0

• 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'-diphenyl-5,5'-bisbenzimidazolyl ether
• 英文别名: 5,5'-oxy-bis(2-phenyl-1H-benzimidazole)；6,6'-oxybis(2-phenyl-1H-benzimidazole)；2-phenyl-6-[(2-phenyl-3H-benzimidazol-5-yl)oxy]-1H-benzimidazole
• CAS: 73672-91-0
• 化学式: C₂₆H₁₈N₄O
• mdl: MFCD03819623
• 分子量: 402.455
• InChiKey: WKXRIOWEJGUTQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,4'-二氨基二苯醚 在 10% Pd/C 、 水 、 氢气 、 硝酸 、 sodium hydrogensulfite 、 溶剂黄146 、 potassium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 8.0h， 生成 2,2'-diphenyl-5,5'-bisbenzimidazolyl ether
  参考文献：
  名称：

  Newly synthesized bis-benzimidazole derivatives exerting anti-tumor activity through induction of apoptosis and autophagy

  摘要：

  In this study, a new series of bis-benzimidazole derivatives were designed and synthesized. Most of these new compounds showed significant anti-tumor activity in vitro compared to Hoechst 33258. Among them, the most potent compound 8 had the IC50 values of 0.56 mu M for HL60 (Human promyelocytic leukemia cells) tumor cell line and 0.58 mu M for U937 (Human leukemic monocyte lymphoma cells) tumor cell line. Subsequent toxicity study on human peripheral blood mononuclear cells (PBMC) showed that compound 8 exhibited less toxicity than 5-FU. We also found that apoptosis and autophagy were simultaneously induced by compound 8 in HL60 cells, and inhibition of autophagy by 3-MA decreased compound 8-induced apoptosis, indicating that they acted in synergy to exert tumor cell death. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.102

文献信息

• Convenient Synthesis of 2-Arylbenzimidazoles and 2,2′-Diaryl-<b><i>bis</i></b>benzimidazoles
  作者：J. Y. Hao、Z. Y. Ge、S. Y. Yang

  DOI：10.1081/scc-120015562

  日期：2003.3

  2-Aryl-benzimidazoles and 2,2'-diaryl-5,5'-bisbenzimidazoles were synthesized conveniently by treating of trifluoromethyl aryl ketones with ortho-diamines in polar solvents with good to excellent yields. The reaction condition is mild and tolerant to most function groups.
• KORSHAK V. V.; GVERDTSITELI I. M.; KIPIANI L. G.; TABIDZE R. S.; LEKAS T.+, IZV. AN GRUZSSR. CEP. XIM., 1979, 5, HO 3, 210-216
  作者：KORSHAK V. V.、 GVERDTSITELI I. M.、 KIPIANI L. G.、 TABIDZE R. S.、 LEKAS T.+

  DOI：——

  日期：——
• Newly synthesized bis-benzimidazole derivatives exerting anti-tumor activity through induction of apoptosis and autophagy
  作者：Xiu-Jun Wang、Na-Ying Chu、Qin-He Wang、Chao Liu、Chun-guo Jiang、Xiao-Yu Wang、Takashi Ikejima、Mao-Sheng Cheng

  DOI：10.1016/j.bmcl.2012.06.102

  日期：2012.10

  In this study, a new series of bis-benzimidazole derivatives were designed and synthesized. Most of these new compounds showed significant anti-tumor activity in vitro compared to Hoechst 33258. Among them, the most potent compound 8 had the IC50 values of 0.56 mu M for HL60 (Human promyelocytic leukemia cells) tumor cell line and 0.58 mu M for U937 (Human leukemic monocyte lymphoma cells) tumor cell line. Subsequent toxicity study on human peripheral blood mononuclear cells (PBMC) showed that compound 8 exhibited less toxicity than 5-FU. We also found that apoptosis and autophagy were simultaneously induced by compound 8 in HL60 cells, and inhibition of autophagy by 3-MA decreased compound 8-induced apoptosis, indicating that they acted in synergy to exert tumor cell death. (C) 2012 Elsevier Ltd. All rights reserved.