5-(3-carboxybenzoyl)-2-hydroxybenzenepropanoic acid | 117424-80-3

• 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: 5-(3-carboxybenzoyl)-2-hydroxybenzenepropanoic acid
• 英文别名: 5-(carboxybenzoyl)-2-hydroxybenzenepropanoic acid；3-[3-(2-carboxyethyl)-4-hydroxybenzoyl]benzoic acid
• CAS: 117424-80-3
• 化学式: C₁₇H₁₄O₆
• 分子量: 314.295
• InChiKey: KZHZVUMMOWZZII-UHFFFAOYSA-N

物化性质

• 熔点：
  197-200 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  629.4±55.0 °C(Predicted)
• 密度：
  1.412±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 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：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(3-carboxybenzoyl)-2-hydroxybenzenepropanoic acid 在 氢氧化钾 、 硫酸 、 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 97.5h， 生成 LY223982
  参考文献：
  名称：

  Benzophenone dicarboxylic acid antagonists of leukotriene B4. 2. Structure-activity relationships of the lipophilic side chain

  摘要：

  A series of lipophilic benzophenone dicarboxylic acid derivatives were found to inhibit the binding of the potent chemotaxin leukotriene B4 (LTB4) to its receptor on intact human neutrophils. Activity at the LTB4 receptor was determined by using a [3H]LTB4-binding assay. The structure-activity relationship for the lipophilic side chain was systematically investigated. Compounds with n-alkyl side chains of varying lengths were prepared and tested. Best inhibition of [3H]LTB4 binding was observed with the n-decyl derivative. Analogues with alkyl chains terminated with an aromatic ring showed improved activity. The 6-phenylhexyl side chain was optimal. Substitution on the terminal aromatic ring was also evaluated. Methoxyl, methylsulfinyl, and methyl substituents greatly enhanced the activity of the compound. For a given substituent, the para isomer had the best activity. Thus the nature of the lipophilic side chain can greatly influence the ability of the compounds to inhibit the binding of LTB4 to its receptor on intact human neutrophils. The most active compound from this series, 84 (LY223982), bound to the LTB4 receptor with an affinity approaching that of the agonist.

  DOI：

  10.1021/jm00172a020
• 作为产物：
  描述：

  乙基3-(2-甲氧基苯基)丙酸酯 在 三氯化铝 、 吡啶盐酸盐 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 5-(3-carboxybenzoyl)-2-hydroxybenzenepropanoic acid
  参考文献：
  名称：

  Benzophenone dicarboxylic acid antagonists of leukotriene B4. 1. Structure-activity relationships of the benzophenone nucleus

  摘要：

  A series of lipophilic benzophenone dicarboxylic acid derivatives was prepared which inhibited the binding of the potent chemotaxin leukotriene B4 to its receptor(s) on intact human neutrophils. With a radioligand-binding assay as a measure of receptor affinity, a structure-activity relationship for this series was investigated. Both acidic residues were required for receptor-binding activity. The relative orientation of the two acidic groups was important for optimal binding. Replacement of the carbonyl group of the benzophenone with a variety of polar and nonpolar linking groups led to only small changes in binding affinity, indicating the linking group may not be involved in receptor recognition. Further structure-activity relationships within this series are reported in an accompanying paper.

  DOI：

  10.1021/jm00172a019

文献信息

• Intermediates for leukotriene antagonists
  申请人：Eli Lilly and Company

  公开号：US04992576A1

  公开（公告）日：1991-02-12

  This invention provides benzene derivatives which are leukotriene antagonists, formulations of those derivatives, intermediates for preparing the derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.

  本发明提供了苯并衍生物，其为白三烯拮抗剂，还提供了这些衍生物的配方、用于制备这些衍生物的中间体以及使用这些衍生物治疗白三烯过度释放引起的病症的方法。
• Leukotriene antagonists
  申请人：Eli Lilly and Company

  公开号：US05171882A1

  公开（公告）日：1992-12-15

  This invention provides benzene derivatives which are leukotriene antagonists, formulations of those derivatives, intermediates for preparing the derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.

  该发明提供了苯衍生物，它们是白三烯拮抗剂，这些衍生物的配方，用于制备这些衍生物的中间体，以及使用这些衍生物治疗白三烯过度释放引起的疾病的方法。
• J. Med. Chem. 1990, 33, 2807-2813
  作者：

  DOI：——

  日期：——
• GAPINSKI, D. MARK;MALLETT, BARBARA E.;FROELICH, LARRY L.;JACKSON, WILLIAM+, J. MED. CHEM., 33,(1990) N0, C. 2798-2807
  作者：GAPINSKI, D. MARK、MALLETT, BARBARA E.、FROELICH, LARRY L.、JACKSON, WILLIAM+

  DOI：——

  日期：——
• GAPINSKI, D. MARK;MALLETT, BARBARA E.;FROELICH, LARRY L.;JACKSON, WILLIAM+, J. MED. CHEM., 33,(1990) N0, C. 2807-2813
  作者：GAPINSKI, D. MARK、MALLETT, BARBARA E.、FROELICH, LARRY L.、JACKSON, WILLIAM+

  DOI：——

  日期：——