(E)-N'-((6-methyl-2-(p-tolyloxy)quinolin-3-yl)methylene)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide | 1594986-96-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (E)-N'-((6-methyl-2-(p-tolyloxy)quinolin-3-yl)methylene)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide
• 英文别名: N-[(E)-[6-methyl-2-(4-methylphenoxy)quinolin-3-yl]methylideneamino]-2-(2-methyl-5-nitroimidazol-1-yl)acetamide
• CAS: 1594986-96-5
• 化学式: C₂₄H₂₂N₆O₄
• 分子量: 458.476
• InChiKey: ROYUJUFXDGQEMG-RPPGKUMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-甲基-5-硝基-1H-咪唑-1-乙酸乙酯 在 nickel(II) nitrate hexahydrate 、 肼 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 (E)-N'-((6-methyl-2-(p-tolyloxy)quinolin-3-yl)methylene)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide
  参考文献：
  名称：

  Schiff’s base derivatives bearing nitroimidazole and quinoline nuclei: New class of anticancer agents and potential EGFR tyrosine kinase inhibitors

  摘要：

  New Schiff's base derivatives 5a-j have been synthesized by reaction between 2-phenoxyquinoline-3-carbaldehydes 3a-j and 2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide 4 in presence of nickel(II) nitrate as a catalyst in ethanol under reflux in good yield (78-92%). All compounds were tested for anticancer and inhibition of EGFR. Of the compounds studied, majority of the compounds showed effective antiproliferation and inhibition of EGFR and HER-2 activities. Compound 5h showed most effective inhibition (IC50 = 0.12 +/- 0.05 mu M) by binding in to the active pocket of EGFR receptor with minimum binding energy (Delta G(b) = -58.3691 kcal/mol). The binding was stabilized by two hydrogen bonds, two pi-cation and one pi-sigma interactions. Compound 5d showed most effective inhibition (IC50 = 0.37 +/- 0.04 mu M). (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.041

文献信息

• Schiff’s base derivatives bearing nitroimidazole and quinoline nuclei: New class of anticancer agents and potential EGFR tyrosine kinase inhibitors
  作者：Jigar A. Makawana、Chetan B. Sangani、Lin Lin、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2014.02.041

  日期：2014.4

  New Schiff's base derivatives 5a-j have been synthesized by reaction between 2-phenoxyquinoline-3-carbaldehydes 3a-j and 2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide 4 in presence of nickel(II) nitrate as a catalyst in ethanol under reflux in good yield (78-92%). All compounds were tested for anticancer and inhibition of EGFR. Of the compounds studied, majority of the compounds showed effective antiproliferation and inhibition of EGFR and HER-2 activities. Compound 5h showed most effective inhibition (IC50 = 0.12 +/- 0.05 mu M) by binding in to the active pocket of EGFR receptor with minimum binding energy (Delta G(b) = -58.3691 kcal/mol). The binding was stabilized by two hydrogen bonds, two pi-cation and one pi-sigma interactions. Compound 5d showed most effective inhibition (IC50 = 0.37 +/- 0.04 mu M). (c) 2014 Elsevier Ltd. All rights reserved.