2-acetyloxybenzoic acid 2-hydroxymethylphenyl ester | 850341-99-0

• 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-acetyloxybenzoic acid 2-hydroxymethylphenyl ester
• 英文别名: [2-(Hydroxymethyl)phenyl] 2-acetyloxybenzoate
• CAS: 850341-99-0
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: WIZYVQRQWSGNLS-UHFFFAOYSA-N

物化性质

• 沸点：
  500.8±40.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-acetyloxybenzoic acid 2-hydroxymethylphenyl ester 在 氯化亚砜 作用下， 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 palladium on activated charcoal 吡啶 、 氯化亚砜 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 2-acetyloxybenzoic acid 2-hydroxymethylphenyl ester
  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

• Quinone-Induced Activation of Keap1/Nrf2 Signaling by Aspirin Prodrugs Masquerading as Nitric Oxide
  作者：Tareisha Dunlap、Sujeewa C. Piyankarage、Gihani T. Wijewickrama、Samer Abdul-Hay、Michael Vanni、Vladislav Litosh、Jia Luo、Gregory R. J. Thatcher

  DOI：10.1021/tx3003609

  日期：2012.12.17

  The promising therapeutic potential of the NO-donating hybrid aspirin prodrugs (NO-ASA) includes induction of chemopreventive mechanisms and has been reported in almost 100 publications. One example, NCX-4040 (pNO-ASA), is bioactivated by esterase to a quinone methide (QM) electrophile. In cell cultures, pNO-ASA and QM-donating X-ASA prodrugs that cannot release NO rapidly depleted intracellular GSH and caused DNA damage; however, induction of Nrf2 signaling elicited cellular defense mechanisms including upregulation of NAD(P)H:quinone oxidoreductase-1 (NQO1) and glutamate-cysteine ligase (GCL). In HepG2 cells, the "NO-specific" 4,5-diaminofluorescein reporter, DAF-DA, responded to NO-ASA and X-ASA, with QM-induced oxidative stress masquerading as NO. LC-MS/MS analysis demonstrated efficient alkylation of Cys residues of proteins including glutathione-S-transferase-P1 (GST-P1) and Kelch-like ECH-associated protein 1 (Keap1). Evidence was obtained for alkylation of Keap1 Cys residues associated with Nrf2 translocation to the nucleus, nuclear translocation of Nrf2, activation of antioxidant response element (ARE), and upregulation of cytoprotective target genes. At least in cell culture, pNO-ASA acts as a QM donor, bioactivated by cellular esterase activity to release salicylates, NO3-, and an electrophilic QM. Finally, two novel aspirin prodrugs were synthesized, both potent activators of ARE, designed to release only the QM and salicylates on bioactivation. Current interest in electrophilic drugs acting via Nrf2 signaling suggests that QM-donating hybrid drugs can be designed as informative chemical probes in drug discovery.
• COMPOUNDS USEFUL IN THE TREATMENT OF NEOPLASTIC DISEASES
  申请人：UNIVERSITÄT ZU KÖLN

  公开号：US20160237023A1

  公开（公告）日：2016-08-18

  Compounds and pharmaceutically acceptable salts of the compounds are useful in the treatment of neoplastic diseases or proliferative disorders. The compounds are formulated into pharmaceutical compositions, which can be used in methods of treating neoplastic diseases or proliferative disorders The compounds are useful to treat cancers such as prostate, pancreatic, lung, skin, breast, bladder, colon, and blood cancers. The compounds are represented by the following formula:
• 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.