3-(4-carboxy-butyryl)-2-hydroxy-benzoic acid methyl ester | 1186308-28-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-carboxy-butyryl)-2-hydroxy-benzoic acid methyl ester
• CAS: 1186308-28-0
• 化学式: C₁₃H₁₄O₆
• 分子量: 266.251
• InChiKey: VJLCTCOFUMIACI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  100.9
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(4-carboxy-butyryl)-2-hydroxy-benzoic acid methyl ester 在 三乙基硅烷 、 三氟乙酸 作用下， 以79%的产率得到3-(4-carboxy-butyl)-2-hydroxy-benzoic acid methyl ester
  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
• 作为产物：
  描述：

  戊二酸酐 、 水杨酸甲酯 在 aluminum (III) chloride 作用下， 以 1,1,2,2-四氯乙烷 为溶剂， 以29%的产率得到3-(4-carboxy-butyryl)-2-hydroxy-benzoic acid methyl ester
  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