5,5'-oxy-bis[2-(3'-methoxy-4'-hydroxyphenyl)-1H-benzimidazole] | 1403460-72-9

• 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: 5,5'-oxy-bis[2-(3'-methoxy-4'-hydroxyphenyl)-1H-benzimidazole]
• 英文别名: 4-[6-[[2-(4-hydroxy-3-methoxyphenyl)-3H-benzimidazol-5-yl]oxy]-1H-benzimidazol-2-yl]-2-methoxyphenol
• CAS: 1403460-72-9
• 化学式: C₂₈H₂₂N₄O₅
• 分子量: 494.506
• InChiKey: KJEFAVKZCNVELV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N,N-(氧代二-4,1-亚苯基)二乙酰胺 在 10% Pd/C 、 水 、 氢气 、 硝酸 、 sodium hydrogensulfite 、 溶剂黄146 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 5,5'-oxy-bis[2-(3'-methoxy-4'-hydroxyphenyl)-1H-benzimidazole]
  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

• 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.