4-(3,4,5-trimethoxybenzyloxy)benzohydrazide

• 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: 4-(3,4,5-trimethoxybenzyloxy)benzohydrazide
• 英文别名: 4-[(3,4,5-Trimethoxyphenyl)methoxy]benzohydrazide；4-[(3,4,5-trimethoxyphenyl)methoxy]benzohydrazide
• 化学式: C₁₇H₂₀N₂O₅
• 分子量: 332.356
• InChiKey: PYCJBABORWXQMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  92
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(3,4,5-trimethoxybenzyloxy)benzohydrazide 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 48.0h， 生成 2-(4-methoxyphenyl)-5-((5-(4-(3,4,5-trimethoxybenzyloxy)phenyl)-1,3,4-oxadiazol-2-ylthio)methyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  带有3,4,5-三甲氧基部分的共轭低聚芳香化合物：其抗氧化活性的研究与DFT研究相关。

  摘要：

  合成了一系列带有众所周知的清除3,4,5-三甲氧基苄氧基的自由基的杂环化合物。将关键化合物4-（3,4,5-三甲氧基苄基氧基）苯并酰肼转化为硫代氨基脲衍生物，随后将其用NaOH环化，得到1,2,4-三唑衍生物。在KOH存在下用二硫化碳替代酰肼，得到相应的1,3,4-恶二唑和各种烷基化衍生物。对新合成的化合物进行纯化，并根据其分析和光谱数据对产物的结构进行阐明和确认。使用2,2-二苯基-1-吡咯肼基（DPPH（•））和铁还原抗氧化能力（FRAP）分析评估了它们的抗氧化活性。硫代氨基脲衍生物在两种抗氧化剂测定中均具有很高的活性，对于DPPH自由基清除具有最低的IC50值。进行了基于密度泛函理论（DFT）的理论计算，以了解NH，SH和CH氢对这些化合物的自由基清除活性的相对重要性。

  DOI：

  10.3390/molecules21020224
• 作为产物：
  描述：

  5-溴甲基-1,2,3-三甲氧基苯 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 30.0h， 生成 4-(3,4,5-trimethoxybenzyloxy)benzohydrazide
  参考文献：
  名称：

  Correlation of antioxidant activities with theoretical studies for new hydrazone compounds bearing a 3,4,5-trimethoxy benzyl moiety

  摘要：

  A new series of antioxidants, namely imines bearing the well-known free radical scavenger group 3,4,5-trimethoxybenzyloxy, was designed and synthesized. Theoretical calculations based on density functional theory (DFT) were performed to understand the antioxidant activities. Experimental studies evaluating the antioxidant activities of the compounds using DPPH and FRAP assays verified the predictions obtained by DMO12 based on DFT.1. The DPPH radical scavenging activities depended on the substitution pattern of the aromatic aldehyde, with both the substitution type and position showing significant effects. Compounds 7b, 7c and 7d, which contain a phenolic hydroxyl group at the para position to the imine as well as, additional electron donating groups at the ortho-position to this hydroxyl group, exhibited IC50 values of 62, 75 and 106 mu g/mL, respectively, and potent antioxidant activities against DPPH, which were better than that of the reference compound BHT. With the exception of compounds 7a and 7h with a phenolic hydroxyl group at the ortho position, all of the investigated compounds exhibited ferric reducing activities above 1000 mu M. Correlation analysis between the two antioxidant assays revealed moderate positive correlation (r = 0.59), indicating differing antioxidant activities based on the reaction mechanism. Therefore, imines bearing a 3,4,5-trimethoxybenzyloxy group can be proposed as potential antioxidants for tackling oxidative stress. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.016

文献信息

• Conjugated Oligo-Aromatic Compounds Bearing a 3,4,5-Trimethoxy Moiety: Investigation of Their Antioxidant Activity Correlated with a DFT Study
  作者：Huda. Kareem、Nurdiana Nordin、Thorsten Heidelberg、Azlina Abdul-Aziz、Azhar Ariffin

  DOI：10.3390/molecules21020224

  日期：——

  A series of heterocyclic compounds bearing the well-known free radical scavenging 3,4,5-trimethoxybenzyloxy group, was synthesized. The key compound 4-(3,4,5-trimethoxybenzyl-oxy)benzohydrazide was converted into thiosemicarbazide derivatives, which were subsequently cyclized with NaOH to provide 1,2,4-triazole derivatives. Alternative treatment of the acid hydrazide with carbon disulfide in the presence

  合成了一系列带有众所周知的清除3,4,5-三甲氧基苄氧基的自由基的杂环化合物。将关键化合物4-（3,4,5-三甲氧基苄基氧基）苯并酰肼转化为硫代氨基脲衍生物，随后将其用NaOH环化，得到1,2,4-三唑衍生物。在KOH存在下用二硫化碳替代酰肼，得到相应的1,3,4-恶二唑和各种烷基化衍生物。对新合成的化合物进行纯化，并根据其分析和光谱数据对产物的结构进行阐明和确认。使用2,2-二苯基-1-吡咯肼基（DPPH（•））和铁还原抗氧化能力（FRAP）分析评估了它们的抗氧化活性。硫代氨基脲衍生物在两种抗氧化剂测定中均具有很高的活性，对于DPPH自由基清除具有最低的IC50值。进行了基于密度泛函理论（DFT）的理论计算，以了解NH，SH和CH氢对这些化合物的自由基清除活性的相对重要性。
• Correlation of antioxidant activities with theoretical studies for new hydrazone compounds bearing a 3,4,5-trimethoxy benzyl moiety
  作者：Huda S. Kareem、Azhar Ariffin、Nurdiana Nordin、Thorsten Heidelberg、Azlina Abdul-Aziz、Kin Weng Kong、Wageeh A. Yehye

  DOI：10.1016/j.ejmech.2015.09.016

  日期：2015.10

  A new series of antioxidants, namely imines bearing the well-known free radical scavenger group 3,4,5-trimethoxybenzyloxy, was designed and synthesized. Theoretical calculations based on density functional theory (DFT) were performed to understand the antioxidant activities. Experimental studies evaluating the antioxidant activities of the compounds using DPPH and FRAP assays verified the predictions obtained by DMO12 based on DFT.1. The DPPH radical scavenging activities depended on the substitution pattern of the aromatic aldehyde, with both the substitution type and position showing significant effects. Compounds 7b, 7c and 7d, which contain a phenolic hydroxyl group at the para position to the imine as well as, additional electron donating groups at the ortho-position to this hydroxyl group, exhibited IC50 values of 62, 75 and 106 mu g/mL, respectively, and potent antioxidant activities against DPPH, which were better than that of the reference compound BHT. With the exception of compounds 7a and 7h with a phenolic hydroxyl group at the ortho position, all of the investigated compounds exhibited ferric reducing activities above 1000 mu M. Correlation analysis between the two antioxidant assays revealed moderate positive correlation (r = 0.59), indicating differing antioxidant activities based on the reaction mechanism. Therefore, imines bearing a 3,4,5-trimethoxybenzyloxy group can be proposed as potential antioxidants for tackling oxidative stress. (C) 2015 Elsevier Masson SAS. All rights reserved.