(2-Formylphenyl) 2-acetyloxybenzoate | 203065-54-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: (2-Formylphenyl) 2-acetyloxybenzoate
• CAS: 203065-54-7
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: HETDJPCJDLSYGO-UHFFFAOYSA-N

物化性质

• 沸点：
  490.8±30.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-Formylphenyl) 2-acetyloxybenzoate 在 palladium on activated charcoal 氯化亚砜 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 [2-(Chloromethyl)phenyl] 2-acetyloxybenzoate
  参考文献：
  名称：

  Nitric oxide-donating non-steroidal anti-inflammatory drugs: the case of nitroderivatives of aspirin

  摘要：

  Nitric oxide (NO) acts as a key signalling mechanism in a number of cells and tissues in the mammalian organism. Modulation of the biosynthesis of NO has emerged to be relevant to the treatment of a variety of human diseases. In the attempt to reduce the serious side effects of non-steroidal anti-inflammatory drugs (NSAIDs), especially in the gastrointestinal tract, a NO-releasing moiety has been linked to conventional NSAIDs. A prototypical example is that of NO-releasing derivatives of aspirin. Thanks to the cytoprotective action of NO such compounds do not produce gastric damage and are emerging as an interesting novel group of drugs for their unique pharmacological properties. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00055-2
• 作为产物：
  描述：

  阿司匹林 在 吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2-Formylphenyl) 2-acetyloxybenzoate
  参考文献：
  名称：

  Nitric oxide-donating non-steroidal anti-inflammatory drugs: the case of nitroderivatives of aspirin

  摘要：

  Nitric oxide (NO) acts as a key signalling mechanism in a number of cells and tissues in the mammalian organism. Modulation of the biosynthesis of NO has emerged to be relevant to the treatment of a variety of human diseases. In the attempt to reduce the serious side effects of non-steroidal anti-inflammatory drugs (NSAIDs), especially in the gastrointestinal tract, a NO-releasing moiety has been linked to conventional NSAIDs. A prototypical example is that of NO-releasing derivatives of aspirin. Thanks to the cytoprotective action of NO such compounds do not produce gastric damage and are emerging as an interesting novel group of drugs for their unique pharmacological properties. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00055-2

文献信息

• Prodrugs — Part 1. Formylphenyl esters of aspirin
  作者：K Bowden、A.P. Huntington、S.L. Powell

  DOI：10.1016/s0223-5234(97)89642-0

  日期：1998.12
• Prodrugs Part 31. 2-Formylphenyl esters of indomethacin, ketoprofen and ibuprofen and 6-substituted 2-formyl and 2-acylphenyl esters of aspirin
  作者：Evelyn A. Abordo、Keith Bowden、Anthony P. Huntington、Sarah L. Powell

  DOI：10.1016/s0014-827x(97)00014-1

  日期：1998.2

  The synthesis and study of a novel series of potential prodrugs of indomethacin, ketoprofen, ibuprofen and aspirin are reported. 2-Formylphenyl esters of the NSAIDs, together with two 6-substituted 2-formyl and two 2-acylphenyl aspirins and 4-formylphenylindomethacin, have been prepared. A study of their alkaline and neutral hydrolysis shows that these compounds, with the exception of 2-acetylphenyl aspirin, act as true prodrugs of the NSAIDs, giving the NSAID and acylphenol. The rates of hydrolysis and activation parameters indicate that the 2-acylphenyl esters employ an intramolecular catalytic route. The 2-formylphenyl testers were more potent as anti-inflammatory agents than the parent compounds in the carragheenan-induced paw oedema test. (C) 1998 Elsevier Science S.A. All rights reserved.
• Nitric oxide-donating non-steroidal anti-inflammatory drugs: the case of nitroderivatives of aspirin
  作者：V Chiroli

  DOI：10.1016/s0223-5234(03)00055-2

  日期：2003.4

  Nitric oxide (NO) acts as a key signalling mechanism in a number of cells and tissues in the mammalian organism. Modulation of the biosynthesis of NO has emerged to be relevant to the treatment of a variety of human diseases. In the attempt to reduce the serious side effects of non-steroidal anti-inflammatory drugs (NSAIDs), especially in the gastrointestinal tract, a NO-releasing moiety has been linked to conventional NSAIDs. A prototypical example is that of NO-releasing derivatives of aspirin. Thanks to the cytoprotective action of NO such compounds do not produce gastric damage and are emerging as an interesting novel group of drugs for their unique pharmacological properties. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.