2-acetyloxybenzoic acid 4-hydroxymethylphenyl ester | 175077-14-2

• 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
• 英文名称: 2-acetyloxybenzoic acid 4-hydroxymethylphenyl ester
• 英文别名: 4-(hydroxymethyl)phenyl 2-acetoxybenzoate；2-(acetyloxy)benzoic acid 4-(hydroxymethyl)phenyl ester；2(acetyloxy) benzoic acid 4(hydroxymethyl)phenyl ester；[4-(Hydroxymethyl)phenyl] 2-acetyloxybenzoate
• CAS: 175077-14-2
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: QHNVBXTVELOXQY-UHFFFAOYSA-N

物化性质

• 熔点：
  106-107 °C
• 沸点：
  469.8±35.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于乙酸乙酯，DCM

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 4-hydroxymethylphenyl ester 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 14.0h， 以57%的产率得到2-(乙酰基氧基)-4-[(硝基氧基)甲基]苯甲酸苯酯
  参考文献：
  名称：

  [EN] COMPOUNDS USEFUL IN THE TREATMENT OF NEOPLASTIC DISEASES
  [FR] COMPOSÉS UTILES DANS LE TRAITEMENT DE MALADIES NÉOPLASIQUES

  摘要：

  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。

  公开号：

  WO2015044177A1
• 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 5.33h， 生成 2-acetyloxybenzoic acid 4-hydroxymethylphenyl 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

• 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。
• [EN] ANTI-INFLAMMATORY COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS ANTI-INFLAMMATOIRES ET LEURS UTILISATIONS
  申请人：RIGAS BASIL

  公开号：WO2009023631A1

  公开（公告）日：2009-02-19

  Compounds of the general Formula (I) are disclosed with activity towards treating diseases related to inflammation, such as cancer, neurodegenerative and cardiovascular diseases. Pharmaceutical compositions and methods of use are also described.

  揭示了通式（I）的化合物，具有治疗与炎症相关的疾病，如癌症、神经退行性和心血管疾病的活性。还描述了制药组合物和使用方法。
• [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。
• NITRODERIVATIVES AS DRUGS FOR DISEASES HAVING AN INFLAMMATORY BASIS
  申请人：DEL SOLDATO Piero

  公开号：US20080194651A1

  公开（公告）日：2008-08-14

  Use for the treatment of diseases having an inflammatory basis of compounds or salts thereof, Having the following general formula (I): A-X 1 -L-(W) p —NO 2 wherein A contains the radical of a drug, X 1 and W are bivalent radicals, L is a covalent bond or oxygen, sulphur, NR 1e wherein R 1e 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，其具有以下通式（I）：A-X1-L-(W)p—NO2，其中A包含药物的基团，X1和W是双价基团，L是共价键或氧，硫，NR1，其中R1是H或C1-C5线性或支链烷基。