1-(4-bromophenyl)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-bromophenyl)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanone
• 英文别名: 1-(4-Bromophenyl)-2-(2-methyl-5-nitroimidazol-1-yl)ethanone
• 化学式: C₁₂H₁₀BrN₃O₃
• 分子量: 324.134
• InChiKey: BYXAGRKOXXWZBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  异烟肼 、 1-(4-bromophenyl)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanone 在 nickel(II) nitrate hexahydrate 作用下， 以 乙醇 为溶剂， 以88%的产率得到(E)-N'-(1-(4-bromophenyl)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethylidene)isonicotinohydrazide
  参考文献：
  名称：

  Schiff’s base derivatives bearing nitroimidazole moiety: New class of antibacterial, anticancer agents and potential EGFR tyrosine kinase inhibitors

  摘要：

  New Schiff's base derivatives 5a-5h have been synthesized by reaction between 1-(4-bromophenyl)-2(2-methyl-5-nitro-1H-imidazol-1-yl) ethanone 3 and various benzohydrazide 4a-4h in presence of nickel (II) nitrate as a catalyst in ethanol at room temperature in good yield (54-88%). All compounds were tested for antibacterial as well as anticancer and inhibition of EGFR. Of the compounds studied, compounds 5d, 5f and 5g in the case of antiproliferation and inhibition of EGFR as well as compounds 5b, 5c, 5e and 5h in the case of antibacterial activity were found to be most effective compounds in the series. Compound 5f shows effective inhibition (IC50 = 0.21 +/- 0.02 mu M) by binding in to the active pocket of EGFR receptor with minimum binding energy (Delta G(b) = - 49.4869 kcal/ mol). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.086
• 作为产物：
  描述：

  2-甲基-4-硝基咪唑 、 2,4'-二溴苯乙酮 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 1-(4-bromophenyl)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanone
  参考文献：
  名称：

  Schiff’s base derivatives bearing nitroimidazole moiety: New class of antibacterial, anticancer agents and potential EGFR tyrosine kinase inhibitors

  摘要：

  New Schiff's base derivatives 5a-5h have been synthesized by reaction between 1-(4-bromophenyl)-2(2-methyl-5-nitro-1H-imidazol-1-yl) ethanone 3 and various benzohydrazide 4a-4h in presence of nickel (II) nitrate as a catalyst in ethanol at room temperature in good yield (54-88%). All compounds were tested for antibacterial as well as anticancer and inhibition of EGFR. Of the compounds studied, compounds 5d, 5f and 5g in the case of antiproliferation and inhibition of EGFR as well as compounds 5b, 5c, 5e and 5h in the case of antibacterial activity were found to be most effective compounds in the series. Compound 5f shows effective inhibition (IC50 = 0.21 +/- 0.02 mu M) by binding in to the active pocket of EGFR receptor with minimum binding energy (Delta G(b) = - 49.4869 kcal/ mol). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.086

文献信息

• Schiff’s base derivatives bearing nitroimidazole moiety: New class of antibacterial, anticancer agents and potential EGFR tyrosine kinase inhibitors
  作者：Jigar A. Makawana、Juan Sun、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2013.09.086

  日期：2013.12

  New Schiff's base derivatives 5a-5h have been synthesized by reaction between 1-(4-bromophenyl)-2(2-methyl-5-nitro-1H-imidazol-1-yl) ethanone 3 and various benzohydrazide 4a-4h in presence of nickel (II) nitrate as a catalyst in ethanol at room temperature in good yield (54-88%). All compounds were tested for antibacterial as well as anticancer and inhibition of EGFR. Of the compounds studied, compounds 5d, 5f and 5g in the case of antiproliferation and inhibition of EGFR as well as compounds 5b, 5c, 5e and 5h in the case of antibacterial activity were found to be most effective compounds in the series. Compound 5f shows effective inhibition (IC50 = 0.21 +/- 0.02 mu M) by binding in to the active pocket of EGFR receptor with minimum binding energy (Delta G(b) = - 49.4869 kcal/ mol). (C) 2013 Elsevier Ltd. All rights reserved.