7-methoxy-1-methyl-1H-benzo[d]imidazole

• 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: 7-methoxy-1-methyl-1H-benzo[d]imidazole
• 英文别名: 7-Methoxy-1-methylbenzimidazole；7-methoxy-1-methylbenzimidazole
• 化学式: C₉H₁₀N₂O
• 分子量: 162.191
• InChiKey: HVGYEJKWKYMXKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乌洛托品 、 7-methoxy-1-methyl-1H-benzo[d]imidazole 在 三氟乙酸 作用下， 反应 72.0h， 以50.4%的产率得到4-methoxy-7-carbaldehyde-N¹-1H-benzo[d]imidazole
  参考文献：
  名称：

  Synthesis and antiproliferative evaluation of novel benzoimidazole-contained oxazole-bridged analogs of combretastatin A-4

  摘要：

  A series of novel oxazole-bridged analogs of combretastatin A-4 bearing a benzo[d]-imidazole as B ring were synthesized and evaluated for antiproliferative activities against five human cancer cell lines. Among all the synthesized compounds, the N-unsubstituted benzoimidazole analog 5 and the analogs 6b, 7a and 7b with a small hydrophobic group on nitrogen atom of benzoimidazole ring were identified as the most potent inhibitors of tumor cell growth with IC50 values at nanomolar levels (5, IC50 = 8.4 nM, HT29; 6b, 7a, 7b, IC50 = 9.6 nM, 3.8 nM, 3.0 nM, A549). In a murine H22 tumor xenograft model, compound 5 exhibited significant antitumor activity. The binding mode of compound 5 in the colchicine binding site of tubulin was probed. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.006
• 作为产物：
  描述：

  2-甲氧基-N-甲基-6-硝基苯胺 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 7-methoxy-1-methyl-1H-benzo[d]imidazole
  参考文献：
  名称：

  Synthesis and antiproliferative evaluation of novel benzoimidazole-contained oxazole-bridged analogs of combretastatin A-4

  摘要：

  A series of novel oxazole-bridged analogs of combretastatin A-4 bearing a benzo[d]-imidazole as B ring were synthesized and evaluated for antiproliferative activities against five human cancer cell lines. Among all the synthesized compounds, the N-unsubstituted benzoimidazole analog 5 and the analogs 6b, 7a and 7b with a small hydrophobic group on nitrogen atom of benzoimidazole ring were identified as the most potent inhibitors of tumor cell growth with IC50 values at nanomolar levels (5, IC50 = 8.4 nM, HT29; 6b, 7a, 7b, IC50 = 9.6 nM, 3.8 nM, 3.0 nM, A549). In a murine H22 tumor xenograft model, compound 5 exhibited significant antitumor activity. The binding mode of compound 5 in the colchicine binding site of tubulin was probed. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.006

文献信息

• Synthesis and antiproliferative evaluation of novel benzoimidazole-contained oxazole-bridged analogs of combretastatin A-4
  作者：Jie Zhou、Jing Jin、Yi Zhang、Yuwen Yin、Xiaoguang Chen、Bailing Xu

  DOI：10.1016/j.ejmech.2013.08.006

  日期：2013.10

  A series of novel oxazole-bridged analogs of combretastatin A-4 bearing a benzo[d]-imidazole as B ring were synthesized and evaluated for antiproliferative activities against five human cancer cell lines. Among all the synthesized compounds, the N-unsubstituted benzoimidazole analog 5 and the analogs 6b, 7a and 7b with a small hydrophobic group on nitrogen atom of benzoimidazole ring were identified as the most potent inhibitors of tumor cell growth with IC50 values at nanomolar levels (5, IC50 = 8.4 nM, HT29; 6b, 7a, 7b, IC50 = 9.6 nM, 3.8 nM, 3.0 nM, A549). In a murine H22 tumor xenograft model, compound 5 exhibited significant antitumor activity. The binding mode of compound 5 in the colchicine binding site of tubulin was probed. (C) 2013 Elsevier Masson SAS. All rights reserved.