ethyl 4-hydroxy-3-(phenylmethoxy)benzoate | 188564-63-8

• 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: ethyl 4-hydroxy-3-(phenylmethoxy)benzoate
• 英文别名: 3-benzyloxy-4-hydroxy-benzoic acid ethyl ester；3-Benzyloxy-4-hydroxy-benzoesaeure-aethylester；Ethyl 3-(benzyloxy)-4-hydroxybenzoate；ethyl 4-hydroxy-3-phenylmethoxybenzoate
• CAS: 188564-63-8
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: GIXTXPIFLIDJHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-hydroxy-3-(phenylmethoxy)benzoate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 3-benzyloxy-4-hydroxy-benzoic acid
  参考文献：
  名称：

  多底物抑制4-羟基苯甲酸酯3-单加氧酶。

  摘要：

  DOI：

  10.1021/jm00050a004
• 作为产物：
  描述：

  4-羟基 3-(苯基甲氧基)苯甲醛 在 硫酸 、 silver(l) oxide 作用下， 生成 ethyl 4-hydroxy-3-(phenylmethoxy)benzoate
  参考文献：
  名称：

  Reactions of Vanillin and its Derived Compounds. XXI.¹ Amides of Vanillic and 3-Ethoxy-4-hydroxybenzoic Acids^2,3

  摘要：

  DOI：

  10.1021/ja01107a021

文献信息

• New aromatic inhibitors of EPSP synthase incorporating hydroxymalonates as novel 3-phosphate replacements
  作者：Ajit Shah、Jose L. Font、Michael J. Miller、Joel E. Ream、Mark C. Walker、James A. Sikorski

  DOI：10.1016/s0968-0896(96)00239-8

  日期：1997.2

  A new, aromatic analogue of the EPSP synthase enzyme reaction intermediate 1 has been identified, which contains a 3-hydroxymalonate moiety in place of the usual 3-phosphate group. This simplified inhibitor was readily prepared in five steps from ethyl 3,4-dihydroxybenzoate. The resulting tetrahedral intermediate mimic 9 is an effective, competitive inhibitor versus S3P with an apparent Ki of 0.57

  已经鉴定出EPSP合酶反应中间体1的新的芳族类似物，其含有3-羟基丙二酸酯部分代替通常的3-磷酸基团。这种简化的抑制剂可以很容易地在5个步骤中由3,4-二羟基苯甲酸乙酯制备。所得的四面体中间体模拟物9是抗S3P的有效竞争性抑制剂，表观Ki为0.57 +/- 0.06 microM。该结果表明3-羟基丙二酸酯显示出与包含先前确定的3-丙二酸酯醚替代物的芳族抑制剂相当的效力，因此可以在该系统中用作合适的3-磷酸酯模拟物。这些新化合物提供了另一个实例，其中在设计EPSP合酶抑制剂时，可以简单地使用简单的苯环代替较复杂的sh草酸酯环。此外，
• Syntheses and characterization of nimesulide derivatives for dual enzyme inhibitors of both cyclooxygenase-1/2 and 5-lipoxygenase
  作者：Yue Li、Shu-Han Chen、Tian-Miao Ou、Jia-Heng Tan、Ding Li、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1016/j.bmc.2011.01.043

  日期：2011.3

  Cyclooxygenase-1/2 (COX-1/2) and 5-lipoxygenase (5-LOX) are enzymes in two different pathways in the inflammatory process. In the present study, a variety of new nimesulide derivatives were synthesized through incorporation of a 5-LOX pharmacophore into nimesulide followed with some structural modifications, which were then characterized for dual enzyme inhibitors for these two types of enzymes. Their structure-activity relationships (SARs) were studied, and compound 20f was found to be an excellent dual enzyme inhibitor. Its binding conformation and interaction mode were studied with molecular docking experiments. Compound 20f could become a lead compound for further development for potential anti-inflammatory drugs. (C) 2011 Elsevier Ltd. All rights reserved.