4-(2-hydroxyethyl)phenyl acetylsalicyloate | 1355183-03-7

• 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: 4-(2-hydroxyethyl)phenyl acetylsalicyloate
• 英文别名: [4-(2-hydroxyethyl)phenyl] 2-acetyloxybenzoate
• CAS: 1355183-03-7
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: BENNDTBUIUJRDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对羟基苯乙醇 、 邻乙酰水杨酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.17h， 以50.6%的产率得到4-(2-hydroxyethyl)phenyl acetylsalicyloate
  参考文献：
  名称：

  Nitric Oxide Release Is Not Required to Decrease the Ulcerogenic Profile of Nonsteroidal Anti-inflammatory Drugs

  摘要：

  The objective of this work was to evaluate the biological properties of a new series of nitric oxide-releasing nonsteroidal anti-inflammatory drugs (NO-NSAIDs) possessing a tyrosol linker between the NSAID and the NO-releasing moiety (PROLI/NO); however, initial screening of ester intermediates without the PROLI/NO group showed the required (desirable) efficacy/safety ratio, which questioned the need for NO in the design. In this regard, NSAID ester intermediates were potent and selective COX-2 inhibitors in vitro, showed equipotent anti-inflammatory activity compared to the corresponding parent NSAID, but showed a markedly reduced gastric toxicity when administered orally. These results provide complementary evidence to challenge the currently accepted notion that hybrid NO-NSAIDs exert their cytoprotective effects by releasing NO. Results obtained in this work constitute a good body of evidence to initiate a debate about the future replacement of NSAID prodrugs for unprotected NSAIDs (possessing a free carboxylic acid group) currently in clinical use.

  DOI：

  10.1021/jm200973j

文献信息

• Nitric Oxide Release Is Not Required to Decrease the Ulcerogenic Profile of Nonsteroidal Anti-inflammatory Drugs
  作者：Sarthak Jain、Susan Tran、Mohamed A. M. El Gendy、Khosrow Kashfi、Paul Jurasz、Carlos A. Velázquez-Martínez

  DOI：10.1021/jm200973j

  日期：2012.1.26

  The objective of this work was to evaluate the biological properties of a new series of nitric oxide-releasing nonsteroidal anti-inflammatory drugs (NO-NSAIDs) possessing a tyrosol linker between the NSAID and the NO-releasing moiety (PROLI/NO); however, initial screening of ester intermediates without the PROLI/NO group showed the required (desirable) efficacy/safety ratio, which questioned the need for NO in the design. In this regard, NSAID ester intermediates were potent and selective COX-2 inhibitors in vitro, showed equipotent anti-inflammatory activity compared to the corresponding parent NSAID, but showed a markedly reduced gastric toxicity when administered orally. These results provide complementary evidence to challenge the currently accepted notion that hybrid NO-NSAIDs exert their cytoprotective effects by releasing NO. Results obtained in this work constitute a good body of evidence to initiate a debate about the future replacement of NSAID prodrugs for unprotected NSAIDs (possessing a free carboxylic acid group) currently in clinical use.