2-acetoxy-3-(4-carboxy-butyryl)-benzoic acid | 1186308-25-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetoxy-3-(4-carboxy-butyryl)-benzoic acid
• 英文别名: 2-Acetyloxy-3-(4-carboxybutanoyl)benzoic acid
• CAS: 1186308-25-7
• 化学式: C₁₄H₁₄O₇
• 分子量: 294.261
• InChiKey: HMFYTZXRCHLKHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-(4-carboxy-butyryl)-2-hydroxy-benzoic acid 、 乙酸酐 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到2-acetoxy-3-(4-carboxy-butyryl)-benzoic acid
  参考文献：
  名称：

  Design, synthesis and evaluation of aspirin analogues having an additional carboxylate substituent for antithrombotic activity

  摘要：

  Acetylsalicylic acid (aspirin) is an effective long-term prophylaxis of thrombotic events such as heart attacks and strokes. It covalently inhibits prostaglandin-H-synthase by interacting with Arg120 or Tyr385 at the active site allowing delivery of its acetyl group to Ser530. However the structure has not been optimized at the active site. We have designed acetylsalicylate analogues with an additional carboxylate substituent which allows simultaneous interaction with Arg120 and Tyr385 whilst positioning the acetyl group in close proximity to Ser530. One of these, an ester derivative which unlike acetylsalicylic acid is non-acidic, may act as useful lead compound for further exploitation of this approach. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.120

文献信息

• Design, synthesis and evaluation of aspirin analogues having an additional carboxylate substituent for antithrombotic activity
  作者：Ahmed Alagha、Edelmiro Moman、Mauro F.A. Adamo、Kevin B. Nolan、Anthony J. Chubb

  DOI：10.1016/j.bmcl.2009.05.120

  日期：2009.8

  Acetylsalicylic acid (aspirin) is an effective long-term prophylaxis of thrombotic events such as heart attacks and strokes. It covalently inhibits prostaglandin-H-synthase by interacting with Arg120 or Tyr385 at the active site allowing delivery of its acetyl group to Ser530. However the structure has not been optimized at the active site. We have designed acetylsalicylate analogues with an additional carboxylate substituent which allows simultaneous interaction with Arg120 and Tyr385 whilst positioning the acetyl group in close proximity to Ser530. One of these, an ester derivative which unlike acetylsalicylic acid is non-acidic, may act as useful lead compound for further exploitation of this approach. (C) 2009 Elsevier Ltd. All rights reserved.