2,4-dimethoxy-N-(4-methoxy-2-nitrophenyl)benzamide | 349107-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4-dimethoxy-N-(4-methoxy-2-nitrophenyl)benzamide
• CAS: 349107-32-0
• 化学式: C₁₆H₁₆N₂O₆
• 分子量: 332.313
• InChiKey: FIRDJSBNTYOPMW-UHFFFAOYSA-N

物化性质

• 沸点：
  452.6±45.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-dimethoxy-N-(4-methoxy-2-nitrophenyl)benzamide 在 盐酸 、 tin(II) chloride dihdyrate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 25.0h， 生成 N-(2-amino-4-methoxyphenyl)-2,4-dimethoxybenzamide hydrochloride
  参考文献：
  名称：

  氨基取代的苯甲酰胺衍生物作为有望的抗氧化剂：结合实验和计算研究。

  摘要：

  我们制备了一系列具有可变数目的甲氧基和羟基的N-芳基苯甲酰胺，带有氨基或氨基质子化的部分，并使用DPPH和FRAP分析来评估其抗氧化能力。相对于参考BHT分子，大多数系统在两种测定法中均表现出改进的抗氧化性能。结合两组实验的结果，三羟基衍生物26显示出最有前途的抗氧化潜能，我们建议将其作为进一步优化苯甲酰胺支架的先导化合物。计算分析有助于解释观察到的趋势，并证明质子化系统比中性系统更好的抗氧化剂，同时潜在于供电子甲氧基对抗氧化剂性能的积极影响，从而证实了实验。还揭示了羟基的引入将酰胺和胺基的反应性移向该部分，并另外增强了抗氧化特性。这在26H •+中尤为明显，这归因于其稳定的[O •···H–O]产生的苯氧基自由基与两个相邻的羟基之间的氢键。我们证明了它的抗氧化活性比不具有N-苯基或不具有酰胺部分的类似三羟基衍生物的抗氧化活性更好，这有力地证明了在设计有效的抗氧化剂中利用双苯基酰胺所采用的策略是合理的。

  DOI：

  10.1021/acs.chemrestox.8b00175
• 作为产物：
  描述：

  2,4-二甲氧基苯甲酸 在 氯化亚砜 、 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 7.0h， 生成 2,4-dimethoxy-N-(4-methoxy-2-nitrophenyl)benzamide
  参考文献：
  名称：

  Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives

  摘要：

  A series of 2-arylbenzimidazole derivatives (3a-3p and 4a-4i) were synthesized and evaluated as potential antioxidant and antimicrobial agents. Their antioxidant properties were evaluated by various in vitro assays including hydroxyl radical (HO center dot) scavenging, superoxide radical anion (O-2(center dot)) scavenging, 1,1-diphenyl- 2-picrylhydrazyl (DPPH) radical scavenging, and ferric reducing antioxidant power. Results demonstrated that compounds with hydroxyl group at the 5-position of benzimidazole ring had a comparable or better antioxidant activity in comparison to standard antioxidant tert-butylhydroquinone (TBHQ). Markedly, compound 4h that showed the highest HO center dot scavenging activity (EC50 = 46 mu M) in vitro had a significant reduction of 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH)-induced intracellular oxidative stress and H2O2-induced cell death. In addition, these compounds showed moderate to good inhibitory activity against Staphylococcus aureus selectively at noncytotoxic concentrations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.004

文献信息

• Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives
  作者：Binhua Zhou、Baojian Li、Wei Yi、Xianzhang Bu、Lin Ma

  DOI：10.1016/j.bmcl.2013.05.004

  日期：2013.7

  A series of 2-arylbenzimidazole derivatives (3a-3p and 4a-4i) were synthesized and evaluated as potential antioxidant and antimicrobial agents. Their antioxidant properties were evaluated by various in vitro assays including hydroxyl radical (HO center dot) scavenging, superoxide radical anion (O-2(center dot)) scavenging, 1,1-diphenyl- 2-picrylhydrazyl (DPPH) radical scavenging, and ferric reducing antioxidant power. Results demonstrated that compounds with hydroxyl group at the 5-position of benzimidazole ring had a comparable or better antioxidant activity in comparison to standard antioxidant tert-butylhydroquinone (TBHQ). Markedly, compound 4h that showed the highest HO center dot scavenging activity (EC50 = 46 mu M) in vitro had a significant reduction of 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH)-induced intracellular oxidative stress and H2O2-induced cell death. In addition, these compounds showed moderate to good inhibitory activity against Staphylococcus aureus selectively at noncytotoxic concentrations. (C) 2013 Elsevier Ltd. All rights reserved.
• Amino-Substituted Benzamide Derivatives as Promising Antioxidant Agents: A Combined Experimental and Computational Study
  作者：Nataša Perin、Petra Roškarić、Irena Sović、Ida Boček、Kristina Starčević、Marijana Hranjec、Robert Vianello

  DOI：10.1021/acs.chemrestox.8b00175

  日期：2018.9.17

  revealed that the introduction of the hydroxy groups shifts the reactivity from both amide and amine groups toward this moiety and additionally enhances antioxidative features. This is particularly evident in 26H•+, which owes its pronounced reactivity to the stabilizing [O•···H–O] hydrogen bonding between the created phenoxyl radical and the two neighboring hydroxy groups. We demonstrated that its

  我们制备了一系列具有可变数目的甲氧基和羟基的N-芳基苯甲酰胺，带有氨基或氨基质子化的部分，并使用DPPH和FRAP分析来评估其抗氧化能力。相对于参考BHT分子，大多数系统在两种测定法中均表现出改进的抗氧化性能。结合两组实验的结果，三羟基衍生物26显示出最有前途的抗氧化潜能，我们建议将其作为进一步优化苯甲酰胺支架的先导化合物。计算分析有助于解释观察到的趋势，并证明质子化系统比中性系统更好的抗氧化剂，同时潜在于供电子甲氧基对抗氧化剂性能的积极影响，从而证实了实验。还揭示了羟基的引入将酰胺和胺基的反应性移向该部分，并另外增强了抗氧化特性。这在26H •+中尤为明显，这归因于其稳定的[O •···H–O]产生的苯氧基自由基与两个相邻的羟基之间的氢键。我们证明了它的抗氧化活性比不具有N-苯基或不具有酰胺部分的类似三羟基衍生物的抗氧化活性更好，这有力地证明了在设计有效的抗氧化剂中利用双苯基酰胺所采用的策略是合理的。