ethyl 5-<(3-carbethoxyphenyl)thio>-2-hydroxybenzenepropanoate | 128950-28-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 5-<(3-carbethoxyphenyl)thio>-2-hydroxybenzenepropanoate
• 英文别名: ethyl 5-(3-carboethoxyphenyl)thio-2-hydroxybenzenepropanate；Ethyl 3-[3-(3-ethoxy-3-oxopropyl)-4-hydroxyphenyl]sulfanylbenzoate
• CAS: 128950-28-7
• 化学式: C₂₀H₂₂O₅S
• 分子量: 374.458
• InChiKey: VBDYLUCAFBEPNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  98.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 5-<(3-carbethoxyphenyl)thio>-2-hydroxybenzenepropanoate 在 氢氧化钾 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 6.5h， 生成 5-<(3-carboxyphenyl)sulfinyl>-2-<(6-phenylhexyl)oxy>benzenepropanoic 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
• 作为产物：
  描述：

  3-(2,2-Diethoxy-chroman-6-ylsulfanyl)-benzoic acid ethyl ester 在 盐酸 、 乙醇 作用下， 反应 0.5h， 以86%的产率得到ethyl 5-<(3-carbethoxyphenyl)thio>-2-hydroxybenzenepropanoate
  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。
• 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：——
• US4992576A
  申请人：——

  公开号：US4992576A

  公开（公告）日：1991-02-12
• US5171882A
  申请人：——

  公开号：US5171882A

  公开（公告）日：1992-12-15
• US5235064A
  申请人：——

  公开号：US5235064A

  公开（公告）日：1993-08-10