(E)-N'-(4-methoxybenzylidene)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide | 1436413-80-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-N'-(4-methoxybenzylidene)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide
• 英文别名: N'-[(1E)-(4-methoxyphenyl)methylene]-2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide；N-[(E)-(4-methoxyphenyl)methylideneamino]-2-(2-methyl-5-nitroimidazol-1-yl)acetamide
• CAS: 1436413-80-7
• 化学式: C₁₄H₁₅N₅O₄
• 分子量: 317.304
• InChiKey: YBELSFNINRGYGL-FRKPEAEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-N'-(4-methoxybenzylidene)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide 、 乙酸酐 以45%的产率得到3-acetyl-2-(4-methoxyphenyl)-5-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-2,3-dihydro-1,3,4-oxadiazole
  参考文献：
  名称：

  Nitroimidazolyl hydrazones are better amoebicides than their cyclized 1,3,4-oxadiazoline analogues: In vitro studies and Lipophilic efficiency analysis

  摘要：

  Two series of compounds with hydrazone derivatives (HZ1-HZ12, series 1) and oxadiazoline derivatives (OZ1-OZ12, series 2) of the 2-methyl-5-nitro-1H-imidazole scaffold were designed and synthesized. Physicochemical properties and Lipophilic efficiency (LipE) analysis predicted higher intrinsic quality of the acylhydrazone derivatives (series 1) than their corresponding oxadiazoline analogues (series 2). In vitro antiamoebic results supported the above findings and validated that the acylhydrazone derivatives (HZ1-HZI2) show better activity than the oxadiazoline derivatives (OZ1-OZ12). MTT assay, using HepG2 cell line, revealed noncytotoxic nature of the compounds. The most promising results were observed for compounds HZ5 (IC50 = 0.96 mu M) and HZ9 (IC50 = 0.81 mu M) both in silico and in vitro. Analysis of the Lipophilic efficiency (LipE) of the compounds provided new insight for the design of potent and selective amoebicides. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.034
• 作为产物：
  描述：

  2-甲基-5-硝基-1H-咪唑-1-乙酸乙酯 在 一水合肼 作用下， 以 甲醇 为溶剂， 生成 (E)-N'-(4-methoxybenzylidene)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide
  参考文献：
  名称：

  塞硝唑衍生物作为潜在的FabH抑制剂的席夫碱的设计，合成和抗菌活性评估

  摘要：

  FabH，β-酮酰基-酰基载体蛋白（ACP）合酶III，对于脂肪酸生物合成的启动至关重要，并且在革兰氏阳性和革兰氏阴性细菌中高度保守。合成了一系列新的塞克硝唑衍生物（1 – 20），并通过光谱法和元素分析对其进行了全面表征。在这些化合物中，6，8，11，13，14，16 - 20报道首次。测试了这些化合物对大肠杆菌，铜绿假单胞菌，枯草芽孢杆菌的抗菌活性和金黄色葡萄球菌。化合物的抑制试验和对接模拟表明，化合物20（E）-2-（2-甲基-5-硝基-1 H-咪唑-1-基）-N' -（3,4,5-三甲基亚苄基）乙酰肼与对被测细菌菌株的MIC为3.13-6.25μg/ mL，是大肠杆菌FabH的有效抑制剂。

  DOI：

  10.1016/j.bmc.2013.03.023

文献信息

• Nitroimidazolyl hydrazones are better amoebicides than their cyclized 1,3,4-oxadiazoline analogues: In vitro studies and Lipophilic efficiency analysis
  作者：Mohmmad Younus Wani、Abdul R. Bhat、Amir Azam、Fareeda Athar

  DOI：10.1016/j.ejmech.2013.03.034

  日期：2013.6

  Two series of compounds with hydrazone derivatives (HZ1-HZ12, series 1) and oxadiazoline derivatives (OZ1-OZ12, series 2) of the 2-methyl-5-nitro-1H-imidazole scaffold were designed and synthesized. Physicochemical properties and Lipophilic efficiency (LipE) analysis predicted higher intrinsic quality of the acylhydrazone derivatives (series 1) than their corresponding oxadiazoline analogues (series 2). In vitro antiamoebic results supported the above findings and validated that the acylhydrazone derivatives (HZ1-HZI2) show better activity than the oxadiazoline derivatives (OZ1-OZ12). MTT assay, using HepG2 cell line, revealed noncytotoxic nature of the compounds. The most promising results were observed for compounds HZ5 (IC50 = 0.96 mu M) and HZ9 (IC50 = 0.81 mu M) both in silico and in vitro. Analysis of the Lipophilic efficiency (LipE) of the compounds provided new insight for the design of potent and selective amoebicides. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Design, synthesis and antimicrobial activities evaluation of Schiff base derived from secnidazole derivatives as potential FabH inhibitors
  作者：Yao Li、Chang-Po Zhao、Hua-Ping Ma、Meng-Yue Zhao、Ya-Rong Xue、Xiao-Ming Wang、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2013.03.023

  日期：2013.6

  antibacterial activities against Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis and Staphylococcus aureus. The compounds inhibitory assay and docking simulation indicated that compound 20 (E)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N′-(3,4,5-trimethylbenzylidene)acetohydrazide with MIC of 3.13–6.25 μg/mL against the tested bacterial strains was a potent inhibitor of Escherichia coli FabH.

  FabH，β-酮酰基-酰基载体蛋白（ACP）合酶III，对于脂肪酸生物合成的启动至关重要，并且在革兰氏阳性和革兰氏阴性细菌中高度保守。合成了一系列新的塞克硝唑衍生物（1 – 20），并通过光谱法和元素分析对其进行了全面表征。在这些化合物中，6，8，11，13，14，16 - 20报道首次。测试了这些化合物对大肠杆菌，铜绿假单胞菌，枯草芽孢杆菌的抗菌活性和金黄色葡萄球菌。化合物的抑制试验和对接模拟表明，化合物20（E）-2-（2-甲基-5-硝基-1 H-咪唑-1-基）-N' -（3,4,5-三甲基亚苄基）乙酰肼与对被测细菌菌株的MIC为3.13-6.25μg/ mL，是大肠杆菌FabH的有效抑制剂。