GM-20

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: GM-20
• 英文别名: [2-(2-Hydroxyethylcarbamoyl)phenyl] acetate；[2-(2-hydroxyethylcarbamoyl)phenyl] acetate
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: FEHXXYYVUWEILN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  C.I.酸性橙108 、 阿司匹林 在 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.42h， 以35.7%的产率得到GM-20
  参考文献：
  名称：

  Reduced mucosal side-effects of acetylsalicylic acid after conjugation with tris-hydroxymethyl-aminomethane. Synthesis and biological evaluation of a new anti-inflammatory compound

  摘要：

  Acetylsalicylic acid (ASA) causes adverse haemorrhagic reactions in the upper gastrointestinal (GI) tract, and previous results have suggested that combination therapy with 2-amino-2-(hydroxymethyl)-1,3-propanediol (Tris) could provide protection in this scenario. Based on this hypothesis, our aim was to develop a new compound from ASA and Tris precursors and to characterize the biological effects of ASA-Tris and the derivatives ASA-bis- and mono-hydroxymethyl-aminomethane (ASA-Bis, ASA-Mono, respectively) using in vivo and in vitro test systems.ASA or ASA conjugates (0.55 mmol/kg, each) were administered intragastrically to Sprague-Dawley rats. Changes in the mucosal structure and in the serosal microcirculation were detected by in vivo imaging techniques, the plasma TNF-alpha, tissue xanthine oxidoreductase and myeloperoxidase activities, and liver cytochrome c changes were also determined. In two separate series, platelet aggregation and carrageenan arthritis-induced inflammatory pain were measured in control, ASA and ASA-Tris-treated groups.Severe mucosal injury and a significant decrease in serosal red blood cell velocity developed in the ASA-treated group and an similar to 2-fold elevation in proinflammatory mediator levels evolved. ASA-Tris did not cause bleeding, microcirculatory dysfunction, mucosal injury or an elevation in proinflammatory markers. The ASA-Mono and ASA-Bis conjugates did not cause macroscopic bleeding, but the inflammatory activation was apparent. ASA-Tris did not influence the cyclooxygenase-induced platelet aggregation significantly, but the inflammatory pain was reduced as effectively as in the case of equimolar ASA doses.ASA-Tris conjugation is an effective approach through which the GI side-effects of ASA are controlled by decreasing the cytokine-mediated progression of pro-inflammatory events. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejphar.2016.04.019

文献信息

• [EN] PHARMACEUTICALLY ACTIVE COMPOUND FOR USE AS ANTI-INFLAMMATORY AGENT<br/>[FR] COMPOSÉ PHARMACEUTIQUEMENT ACTIF UTILISABLE COMME AGENT ANTI-INFLAMMATOIRE
  申请人：PAX FORSCHUNG GMBH

  公开号：WO2015101501A1

  公开（公告）日：2015-07-09

  The present application refers to a medicinally active compound of formula (I) and its possible use as anti-inflammatory agent. Further, the present application refers to a method for the preparation of the compound of formula (I) as well as to a pharmaceutical composition comprising a compound of formula (I).

  本申请涉及一种具有药理活性的公式(I)化合物及其可能用作抗炎剂的应用。此外，本申请还涉及一种制备公式(I)化合物的方法，以及包含公式(I)化合物的药物组合物。
• Pharmaceutically Active Compound for Use as Anti-inflammatory Agent
  申请人：Pax Forschung GmbH

  公开号：US20160326098A1

  公开（公告）日：2016-11-10

  The present application refers to a medicinally active compound of formula (I) and its possible use as anti-inflammatory agent. Further, the present application refers to a method for the preparation of the compound of formula (I) as well as to a pharmaceutical composition comprising a compound of formula (I).