3-(4-羟基苯基)硫烷基苯甲酸 | 128950-13-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 3-(4-羟基苯基)硫烷基苯甲酸
• 中文别名: 苯甲酸,3-[(4-羟基苯基)硫代]-
• 英文名称: 4-<(3-carboxyphenyl)thio>phenol
• 英文别名: 3-(4-hydroxythiophenoxy)benzoic acid；3-[(4-Hydroxyphenyl)sulfanyl]benzoic acid；3-(4-hydroxyphenyl)sulfanylbenzoic acid
• CAS: 128950-13-0
• 化学式: C₁₃H₁₀O₃S
• 分子量: 246.287
• InChiKey: IKZIEHJSODHPOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-羟基苯基)硫烷基苯甲酸 在 盐酸 、 lithium hydroxide 、 乙醇 、 硫酸 、 sodium hydride 、 三甲基乙酸 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 103.0h， 生成 3-[3-(2-Carboxy-ethyl)-4-(6-phenyl-hexyloxy)-phenylsulfanyl]-benzoic 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-[(4-甲氧苯基)硫烷基]苯甲酸 在 吡啶盐酸盐 作用下， 反应 4.0h， 以85%的产率得到3-(4-羟基苯基)硫烷基苯甲酸
  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

• METHOD FOR PRODUCING THIOETHER COMPOUND
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP1806337A1

  公开（公告）日：2007-07-11

  Disclosed is an efficient and widely-applicable method for commercially producing a thioether compound or a thiol compound which is useful as a pharmaceutical compound or a production intermediate of it. Specifically disclosed is a method for producing a thioether compound represented by the general formula [I] below or a salt thereof. This method is characterized in that a compound represented by the following general formula [III]: [III] (wherein X represents a bromine atom, a chlorine atom or a trifluoromethylsulfonyloxy group, and ring A represents an aryl group or a heteroaryl ring group) or a salt thereof is reacted with a thiol compound represented by the following general formula [II]: [II] or a salt thereof in the presence of a palladium compound such as Pd2(dba)3, a base such as i-Pr2NEt and a phosphorus compound represented by the following formula [AA].

  本发明公开了一种用于商业化生产硫醚化合物或硫醇化合物的高效且广泛适用的方法，硫醚化合物或硫醇化合物可用作药物化合物或其生产中间体。具体地说，本发明公开了一种生产以下通式[I]代表的硫醚化合物或其盐的方法。该方法的特征在于由以下通式[III]代表的化合物：[III]（其中 X 代表溴原子、氯原子或三氟甲基磺酰氧基，环 A 代表芳基或杂芳基环基）或其盐与下 列通式[II]代表的硫醇化合物反应：[II]或其盐在钯化合物如 Pd2(dba)3、碱如 i-Pr2NEt 和下式[AA]代表的磷化合物存在下反应。
• Nitrophenyl Derivatives as Aldose Reductase Inhibitors
  作者：Luca Costantino、Anna Maria Ferrari、Maria Cristina Gamberini、Giulio Rastelli

  DOI：10.1016/s0968-0896(02)00318-8

  日期：2002.12

  Nitrophenyl derivatives ere recently discovered as a new class of ALR2 inhibitors by means of docking and database screening of the National Cancer Institute database of organic molecules. The nitro group was predicted to bind to the Tyr48 and His110 active site residues of the enzyme. the site adhere acidic ALR2 inhibitors such as carboxylic acids bind in their anionic form. Given the novelty of these Compounds. we decided to expand their structure-activity relationships by synthesizing and testing a series of derivatives and the corresponding compounds having a carboxylic group instead of the nitro moiety: the results obtained were rationalized by means of docking and molecular dynamics simulations. On the whole there is an agreement between inhibitory data and the results of molecular modeling experiments. supporting the hypothesized binding mode of these compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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：——
• Benzophenone dicarboxylic acid antagonists of leukotriene B4. 1. Structure-activity relationships of the benzophenone nucleus
  作者：D. Mark Gapinski、Barbara E. Mallett、Larry L. Froelich、William T. Jackson

  DOI：10.1021/jm00172a019

  日期：1990.10

  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.