4-(3,4,5-trimethoxyphenyl)-5-(4-methoxy-1H-benzo[d]imidazole-7-yl) oxazole | 1403581-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(3,4,5-trimethoxyphenyl)-5-(4-methoxy-1H-benzo[d]imidazole-7-yl) oxazole
• 英文别名: 5-(7-methoxy-1H-benzimidazol-4-yl)-4-(3,4,5-trimethoxyphenyl)-1,3-oxazole
• CAS: 1403581-29-2
• 化学式: C₂₀H₁₉N₃O₅
• 分子量: 381.388
• InChiKey: SMJXFBKRXYLKRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(3,4,5-trimethoxyphenyl)-5-(4-methoxy-1H-benzo[d]imidazole-7-yl) oxazole 在 水 、 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 氘代丙酮 为溶剂， 反应 20.67h， 生成 4-(3,4,5-trimethoxyphenyl)-5-(7-methoxy-N-carboxymethylbenzo[d]imidazole-4-yl)oxazole
  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-氨基-3-硝基苯酚 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 68.5h， 生成 4-(3,4,5-trimethoxyphenyl)-5-(4-methoxy-1H-benzo[d]imidazole-7-yl) oxazole
  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