2-(乙酰基氧基)-4-[(硝基氧基)甲基]苯甲酸苯酯 | 287118-97-2

• 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-(乙酰基氧基)-4-[(硝基氧基)甲基]苯甲酸苯酯
• 英文名称: [2-(acetyloxy)benzoicacid 4-(nitrooxy methyl)phenyl ester]
• 英文别名: 2-(acetyloxy)benzoic acid 4-(nitrooxymethyl)phenyl ester；2-(acetyl)benzoic acid 4-(nitroxymethyl)phenyl ester；nitric oxide-donating aspirin；nitroaspirin；NCX 4040；NCX-4040；NO-aspirin；[4-(nitrooxymethyl)phenyl] 2-acetyloxybenzoate
• CAS: 287118-97-2
• 化学式: C₁₆H₁₃NO₇
• 分子量: 331.282
• InChiKey: CTHNKWFUDCMLIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  83-86°C
• 沸点：
  495.7±40.0 °C(Predicted)
• 密度：
  1.347±0.06 g/cm3(Predicted)
• 溶解度：
  在DMSO中的溶解度为15mg/mL（澄清溶液）

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 储存条件：
  20°C

制备方法与用途

NCX4040（无阿司匹林）是一种非甾体抗炎药（NSAID），它是阿司匹林的一种一氧化氮(NO)释放形式。研究显示，NCX4040可以诱导PC3转移性前列腺癌细胞凋亡，并具有显著的抗炎和抗癌作用[1]。

反应信息

• 作为产物：
  描述：

  阿司匹林 在 palladium on activated charcoal 吡啶 、 氯化亚砜 、 氢气 、 silver nitrate 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 14.0h， 生成 2-(乙酰基氧基)-4-[(硝基氧基)甲基]苯甲酸苯酯
  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

文献信息

• [EN] COMPOUNDS USEFUL IN THE TREATMENT OF NEOPLASTIC DISEASES<br/>[FR] COMPOSÉS UTILES DANS LE TRAITEMENT DE MALADIES NÉOPLASIQUES
  申请人：UNIVERSITÄT ZU KÖLN

  公开号：WO2015044177A1

  公开（公告）日：2015-04-02

  The present invention refers to compounds of formula: (formula A), wherein R1 is selected from (formula I), (formula II), (formula (III), (formula IV), (formula V), or (formula B), and wherein R2, R3, R4 and R5 are as defined in the claims and X is OTBS, hydroxy, formyloxy, acetoxy, nitrooxy, nitrooxymethyl, or a halogen; and pharmaceutically acceptable salts thereof, which are useful in the treatment of neoplastic or proliferative disorders, a pharmaceutical composition comprising such a compound and a method preparing this compound.

  本发明涉及以下式的化合物：（式A），其中R1从（式I），（式II），（式III），（式IV），（式V）或（式B）中选择，并且其中R2，R3，R4和R5如权利要求中定义的那样，X为OTBS，羟基，甲酰氧基，乙酰氧基，硝基氧基，硝基甲氧基或卤素；及其药学上可接受的盐，用于治疗肿瘤性或增生性疾病，包括这种化合物的药物组合物和制备该化合物的方法。
• Nitroderivatives as drugs for diseases having an inflammatory basis
  申请人：——

  公开号：US20040023933A1

  公开（公告）日：2004-02-05

  Use for the treatment of diseases having an inflammatory basis of compounds or salts thereof, having the following general formula (I): A-X t -L-(W) p —NO 2 wherein A contains the radical of a drug, X t and W arc bivalent radicals, L, is a covalent bond or oxygen, sulphur, NR tc wherein R tc is H or a C 1 -C 5 linear or branched alkyl.

  用于治疗具有炎症基础的疾病的化合物或其盐，具有以下一般公式（I）：A-X t -L-(W) p —NO 2 其中A含有药物的自由基，X t 和W是二价基团，L是共价键或氧、硫、NR tc ，其中R tc 是H或C 1 -C 5 的直链或支链烷基。
• Drugs for diabetes
  申请人：——

  公开号：US20040023890A1

  公开（公告）日：2004-02-05

  Use for the diabetes treatment of compounds or salts thereof, having the following general formula (I): A-(B) b0 —(C) c0 —NO 2 wherein A contains the radical of a drug having an antiiflammatory or analgesic activity, B is a bivalen: linking group wherein the precursor must meet the tests described in the application, C is a a bivalent linking group as defined in the invention.

  用于治疗糖尿病的化合物或其盐，具有如下通用公式（I）：A-(B) b0 —(C) c0 —NO 2 其中A含有具有抗炎或镇痛活性的药物的自由基，B是一个双价连接基团，其中前体必须符合本申请中描述的测试，C是如发明中定义的双价连接基团。
• Hindered Amine Nitric Oxide Donating Polymers for Coating Medical Devices
  申请人：Cheng Peiwen

  公开号：US20070264225A1

  公开（公告）日：2007-11-15

  Disclosed are hindered amine nitric oxide (NO) donating polymers for coating implantable medical devices. The polymers include sterically hindered secondary amines that do not react with monomer carbonyls or electrophilic alkenes, facilitating the synthesis of the NO donating polymers. The polymers are coated on implantable medical devices, providing anti-restenosis therapy by the release of NO at the implantation site.

  本发明涉及一种用于涂覆植入式医疗器械的受阻胺硝酸氧化物（NO）捐赠聚合物。该聚合物包括具有立体位阻的次级胺，不与单体羰基或亲电性烯烃反应，从而便于合成NO捐赠聚合物。该聚合物被涂覆在植入式医疗器械上，在植入部位释放NO，提供抗再狭窄治疗。
• [EN] NITRODERIVATIVES AS DRUGS FOR DISEASES HAVING AN INFLAMMATORY BASIS<br/>[FR] NITRODERIVES UTILES EN TANT QUE MEDICAMENTS DESTINES A DES MALADIES D'ORIGINE INFLAMMATOIRE
  申请人：NICOX SA

  公开号：WO2002030866A1

  公开（公告）日：2002-04-18

  Use for the treatment of diseases having an inflammatory basis of compounds or salts thereof, having the following general formula (I): A-X1-L-(W)p-NO2 wherein A contains the radical of a drug, X1 and W are bivalent radicals, L is a covalent bond or oxygen, sulphur, NR1c wherein R1c is H or a C1-C5 linear or branched alkyl.

  用于治疗具有炎症基础的疾病的化合物或其盐，其具有以下一般式（I）：A-X1-L-(W)p-NO2，其中A包含药物的基团，X1和W是二价基团，L是共价键或氧，硫，NR1c，其中R1c是H或C1-C5线性或支链烷基。