3-Benzoyl-N-hydroxy-benzamide | 125542-22-5

• 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: 3-Benzoyl-N-hydroxy-benzamide
• 英文别名: 3-benzoyl-N-hydroxybenzamide
• CAS: 125542-22-5
• 化学式: C₁₄H₁₁NO₃
• 分子量: 241.246
• InChiKey: LAZDNRBVPKMJSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Benzoyl-N-hydroxy-benzamide 、 丁炔二酸二甲酯 在 sodium acetate 作用下， 以 水 为溶剂， 反应 2.0h， 以90%的产率得到(E)-N-(1,4-dimethoxy-1,4-dioxobutan-2-ylidene)-3-benzoylbenzoic-1-phenylcarboxamide N-oxide
  参考文献：
  名称：

  在水上：由异羟肟酸和二甲基/乙二乙二羧酸二乙酯合成硝基的自由催化方法

  摘要：

  苯氧肟酸在10 mol％NaOAc存在下与乙二酸二甲酯反应生成良好的（E）-N-（1,4-二甲氧基-1,4-二氧代丁烷-2-亚基）-1-苯基羧酰胺氧化物在室温下连续2小时在水中产生水，这提供了一种简单，高效且环境友好的方法来合成各种硝酮。这种策略的好处不仅符合绿色化学的要求，而且具有原子经济性。

  DOI：

  10.1002/cjoc.201300400
• 作为产物：
  描述：

  3-苯甲酰苯甲酸 、 羟胺 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 生成 3-Benzoyl-N-hydroxy-benzamide
  参考文献：
  名称：

  Hydroxamic acid inhibitors of 5-lipoxygenase: quantitative structure-activity relationships

  摘要：

  An evaluation of the quantitative structure-activity relationships (QSAR) for more than 100 hydroxamic acids revealed that the primary physicochemical feature influencing the in vitro 5-lipoxygenase inhibitory potencies of these compounds is the hydrophobicity of the molecule. A significant correlation was observed between the octanol-water partition coefficient of the substituent attached to the carbonyl of the hydroxamate and in vitro inhibitory activity. This correlation held for hydroxamic acids of diverse structure and with potencies spanning 4 orders of magnitude. Although the hydrophobicity may be packaged in a variety of structural ways and still correlate with potency, the QSAR study revealed two major exceptions. Specifically, the hydrophobicity of portions of compounds in the immediate vicinity of the hydroxamic acid functionality does not appear to contribute to increased inhibition and the hydrophobicity of fragments beyond approximately 12 A from the hydroxamate do not influence potency. The QSAR study also demonstrated that inhibitory activity was enhanced when there was an alkyl group on the hydroxamate nitrogen, when electron-withdrawing substituents were present and when the hydroxamate was conjugated to an aromatic system. These observations provide a simple description of the lipoxygenase-hydroxamic acid binding site.

  DOI：

  10.1021/jm00165a017

文献信息

• [EN] SMALL MOLECULE INHIBITORS OF HISTONE DEACTEYLASES<br/>[FR] INHIBITEURS À PETITE MOLÉCULE D'HISTONE DÉSACÉTYLASES
  申请人：NUPOTENTIAL INC

  公开号：WO2013059582A2

  公开（公告）日：2013-04-25

  The disclosure relates to small molecules and methods, compositions, and kits comprising these small molecules. In still another embodiment, the disclosure relates to small molecules that inhibit HDAC activity. In yet another embodiment, the disclosure relates to small molecules for inhibiting the growth of cancer cells. In still another embodiment, the disclosure relates to small molecules for reprogramming a cell.
• Hydroxamic acid inhibitors of 5-lipoxygenase: quantitative structure-activity relationships
  作者：James B. Summers、Ki H. Kim、Hormoz Mazdiyasni、James H. Holms、James D. Ratajczyk、Andrew O. Stewart、Richard D. Dyer、George W. Carter

  DOI：10.1021/jm00165a017

  日期：1990.3

  An evaluation of the quantitative structure-activity relationships (QSAR) for more than 100 hydroxamic acids revealed that the primary physicochemical feature influencing the in vitro 5-lipoxygenase inhibitory potencies of these compounds is the hydrophobicity of the molecule. A significant correlation was observed between the octanol-water partition coefficient of the substituent attached to the carbonyl of the hydroxamate and in vitro inhibitory activity. This correlation held for hydroxamic acids of diverse structure and with potencies spanning 4 orders of magnitude. Although the hydrophobicity may be packaged in a variety of structural ways and still correlate with potency, the QSAR study revealed two major exceptions. Specifically, the hydrophobicity of portions of compounds in the immediate vicinity of the hydroxamic acid functionality does not appear to contribute to increased inhibition and the hydrophobicity of fragments beyond approximately 12 A from the hydroxamate do not influence potency. The QSAR study also demonstrated that inhibitory activity was enhanced when there was an alkyl group on the hydroxamate nitrogen, when electron-withdrawing substituents were present and when the hydroxamate was conjugated to an aromatic system. These observations provide a simple description of the lipoxygenase-hydroxamic acid binding site.
• On Water: Free Catalysis Approach for the Synthesis of Nitrones from Hydroxamic Acids and Dimethy/Diethyl Acetylenedicarboxylate
  作者：Jian Li、Yongqin He、Xiaoyu Ren、Xiaokang Shi、Sizhuo Yang、Xiai Gao、Guosheng Huang

  DOI：10.1002/cjoc.201300400

  日期：2013.8

  Benzohydroxamic acid reacts with dimethyl acetylenedicarboxylate in the presence of 10 mol% NaOAc to generate (E)‐N‐(1,4‐dimethoxy‐1,4‐dioxobutan‐2‐ylidene)‐1‐phenylcarboxamide oxide in good‐to‐excellent yield in water at room temperature for 2 h, which supplies a simple, efficient and environmentally friendly method to synthesize a wide range of nitrones. The benefits of this strategy not only conform

  苯氧肟酸在10 mol％NaOAc存在下与乙二酸二甲酯反应生成良好的（E）-N-（1,4-二甲氧基-1,4-二氧代丁烷-2-亚基）-1-苯基羧酰胺氧化物在室温下连续2小时在水中产生水，这提供了一种简单，高效且环境友好的方法来合成各种硝酮。这种策略的好处不仅符合绿色化学的要求，而且具有原子经济性。