2-(乙酰氧基)苯甲酸3-(羟基甲基)苯基酯 | 287118-98-3

• 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
• 中文名称: 2-(乙酰氧基)苯甲酸3-(羟基甲基)苯基酯
• 英文名称: NCX 4017
• 英文别名: NCX4017；2-(acetyloxy)benzoic acid 3-(hydroxymethyl)phenyl ester；3-(hydroxymethyl)phenyl 2-acetoxybenzoate；[3-(hydroxymethyl)phenyl] 2-acetyloxybenzoate
• CAS: 287118-98-3
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: XYNPCXQRPQWCKP-UHFFFAOYSA-N

物化性质

• 熔点：
  77-79°C
• 沸点：
  473.5±35.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、二氯甲烷

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-(乙酰氧基)苯甲酸3-(羟基甲基)苯基酯 以40的产率得到2-(乙酰氧基)-苯甲酸 3-[(硝基氧基)甲基]苯基酯
  参考文献：
  名称：

  Process for obtaining (nitroxymethyl)phenyl esters of salicylic acid derivatives

  摘要：

  一种获得公式（I）中R1为OCOR3基团的水杨酸衍生物的（亚硝基甲基）苯酯的方法，其特征在于包括以下步骤：a）在碱的存在下，将水杨酸衍生物的卤代物与羟基苯甲醇反应；b）在无水条件下，用硝酸与不同的无机酸、有机酸或一个或两个有机酸的酐混合物对所得产物进行硝化；c）回收最终产物。

  公开号：

  US06696591B1
• 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-(乙酰氧基)苯甲酸3-(羟基甲基)苯基酯
  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。
• Nitric Oxide Releasing Prodrugs of Therapeutic Agents
  申请人：SATYAM Apparao

  公开号：US20110263526A1

  公开（公告）日：2011-10-27

  The present invention relates to nitric oxide releasing prodrugs of known drugs or therapeutic agents which are represented herein as compounds of formula (I) wherein the drugs or therapeutic agents contain one or more functional groups independently selected from a carboxylic acid, an amino, a hydroxyl and a sulfhydryl group. The invention also relates to processes for the preparation of the nitric oxide releasing prodrugs (the compounds of formula (I)), to pharmaceutical compositions containing them and to methods of using the prodrugs.

  本发明涉及已知药物或治疗剂的一氧化氮释放前药，其在此处表示为式(I)的化合物，其中药物或治疗剂包含一个或多个功能基团，独立地选自羧酸、氨基、羟基和巯基。该发明还涉及制备一氧化氮释放前药（式(I)的化合物）的方法，含有它们的药物组合物以及使用这些前药的方法。
• [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。
• 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.
• 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