3-(9,10-Dioxo-9,10-dihydro-anthracen-2-yl)-N-hydroxy-N-methyl-acrylamide | 125542-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-(9,10-Dioxo-9,10-dihydro-anthracen-2-yl)-N-hydroxy-N-methyl-acrylamide
• 英文别名: (E)-3-(9,10-dioxoanthracen-2-yl)-N-hydroxy-N-methylprop-2-enamide
• CAS: 125542-28-1
• 化学式: C₁₈H₁₃NO₄
• 分子量: 307.306
• InChiKey: YJVFEZJUIQWNRX-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-甲基羟胺 、 3t-(9,10-dioxo-9,10-dihydro-[2]anthryl)-acrylic acid 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 生成 3-(9,10-Dioxo-9,10-dihydro-anthracen-2-yl)-N-hydroxy-N-methyl-acrylamide
  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

• 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.