2-(acetyloxy)benzoic acid 3-(chloromethyl) phenyl ester | 287118-99-4

• 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-(acetyloxy)benzoic acid 3-(chloromethyl) phenyl ester
• 英文别名: 2-(acetyloxy)benzoic acid 3-(chloromethyl)-phenyl ester；3-(Chloromethyl)phenyl 2-(acetyloxy)benzoate；[3-(chloromethyl)phenyl] 2-acetyloxybenzoate
• CAS: 287118-99-4
• 化学式: C₁₆H₁₃ClO₄
• 分子量: 304.73
• InChiKey: WLAFKTNYWHOVEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(acetyloxy)benzoic acid 3-(chloromethyl) phenyl ester 在 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 2-(乙酰氧基)-苯甲酸 3-[(硝基氧基)甲基]苯基酯
  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 、 sodium tetrahydroborate 、 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(acetyloxy)benzoic acid 3-(chloromethyl) phenyl ester
  参考文献：
  名称：

  Chemical Insights in the Concept of Hybrid Drugs:  The Antitumor Effect of Nitric Oxide-Donating Aspirin Involves A Quinone Methide but Not Nitric Oxide nor Aspirin

  摘要：

  Hybrid drug 1 (NO-ASA) continues to attract intense research from chemists and biologists alike. It consists of ASA and a -ONO2 group connected through a spacer and is in preclinical development as an antitumor drug. We report that, contrary to current beliefs, neither ASA nor NO contributes to this antitumor effect. Rather, an unsubstituted QM was identified as the sole cytotoxic agent. QM forms from 1 after carboxylic ester hydrolysis and, in accordance with the HSAB theory, selectively reacts with cellular GSH, which in turn triggers cell death. Remarkably, a derivative lacking ASA and the -ONO2 group is 10 times more effective than 1. Thus, our data provide a conclusive molecular mechanism for the antitumor activity of 1. Equally importantly, we show for the first time that a "presumed invisible" linker in a hybrid drug is not so invisible after all and is in fact solely responsible for the biological effect.

  DOI：

  10.1021/jm061371e

文献信息

• Synthesis method of nitroxymethylphenyl esters of aspirin derivatives
  申请人：Nicox S.A.

  公开号：US06512137B1

  公开（公告）日：2003-01-28

  The invention describes a method for the synthesis of nitroxymethylphenyl esters of aspirin derivatives.

  这项发明描述了一种合成阿司匹林衍生物的硝氧甲基苯酯的方法。
• Compounds and compositions for treating dysproliferative diseases, and methods of use thereof
  申请人：Kashfi Khosrow

  公开号：US20050182134A1

  公开（公告）日：2005-08-18

  Compounds are disclosed with activity towards killing dysproliferative cells in vitro and treating cancer in vivo. Cancers such as cancer of the colon, pancreas, prostate, lung, breast, urinary bladder, skin and liver are exemplary. Compounds, pharmaceutical compositions and methods of use are described.

  揭示了具有对体外杀灭异常增殖细胞活性的化合物，并用于治疗体内癌症。癌症如结肠癌、胰腺癌、前列腺癌、肺癌、乳腺癌、膀胱癌、皮肤癌和肝癌是示例。描述了化合物、药物组合物和使用方法。
• [EN] SYNTHESIS METHOD OF NITROXYMETHYLPHENYL ESTERS OF ASPIRIN DERIVATIVES<br/>[FR] SYNTHESE D'ESTERS DE NITROXYMETHYLPHENYLE-ESTERS DE DERIVES DE L'ASPIRINE
  申请人：NICOX SA

  公开号：WO2000044705A1

  公开（公告）日：2000-08-03

  The invention describes a method for the synthesis of nitroxymethylphenyl esters of aspirin derivatives.

  本发明描述了一种合成阿司匹林衍生物的亚硝基甲基苯酯的方法。
• SYNTHESIS METHOD OF NITROXYMETHYLPHENYL ESTERS OF ASPIRIN DERIVATIVES
  申请人：NICOX S.A.

  公开号：EP1147074A1

  公开（公告）日：2001-10-24
• EP1709155A4
  申请人：——

  公开号：EP1709155A4

  公开（公告）日：2007-10-31