4-(3,4,5-trimethoxyphenyl)-5-(7-methoxy-N¹-cyanomethylbenzo[d]imidazole-4-yl)oxazole | 1403581-40-7

• 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-(7-methoxy-N¹-cyanomethylbenzo[d]imidazole-4-yl)oxazole
• 英文别名: 2-[7-Methoxy-4-[4-(3,4,5-trimethoxyphenyl)-1,3-oxazol-5-yl]benzimidazol-1-yl]acetonitrile；2-[7-methoxy-4-[4-(3,4,5-trimethoxyphenyl)-1,3-oxazol-5-yl]benzimidazol-1-yl]acetonitrile
• CAS: 1403581-40-7
• 化学式: C₂₂H₂₀N₄O₅
• 分子量: 420.425
• InChiKey: WEZUBAVUMAMFDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(3,4,5-trimethoxyphenyl)-5-(7-methoxy-N¹-cyanomethylbenzo[d]imidazole-4-yl)oxazole 在 potassium hydroxide 作用下， 以 叔丁醇 为溶剂， 反应 1.0h， 以43%的产率得到4-(3,4,5-trimethoxyphenyl)-5-(7-methoxy-N¹-carbamoylmethylbenzo[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 、 丙酮 为溶剂， 反应 74.5h， 生成 4-(3,4,5-trimethoxyphenyl)-5-(7-methoxy-N¹-cyanomethylbenzo[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

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.