(2R)-3-(4-hydroxyphenyl)-2-phenylpropanoic acid | 178258-43-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2R)-3-(4-hydroxyphenyl)-2-phenylpropanoic acid
• CAS: 178258-43-0
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: GRCCNKUXWQWOKS-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-3-(4-hydroxyphenyl)-2-phenylpropanoic acid 在 N-甲基吗啉 、 吡啶 、 hydroxylamine Wang resin 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (S)-N-hydroxy-3-(4-hydroxyphenyl)-2-phenylpropanamide
  参考文献：
  名称：

  Design and Evaluation of Hydroxamate Derivatives as Metal-Mediated Inhibitors of a Protein Tyrosine Kinase

  摘要：

  Protein tyrosine kinases use two Mg2+ ions as cofactors in catalysis, one as the ATP-Mg complex (M1) and the other as an essential activator (M2). The M2-binding site has high affinity for transition metal cations such as cobalt and zinc. Taking advantage of this high affinity, we examined hydroxamates as metal-mediated inhibitors against C-terminal Src kinase (Csk), a protein tyrosine kinase. Of a small group of amino acid hydroxamates, tyrosine and phenylalanine hydroxamates inhibited Csk activity only in the presence of Co2+. Four classes of phenylalanine and tyrosine hydroxamate derivatives were synthesized and evaluated as metal-mediated inhibitors of Csk, leading to improved inhibition and a better understanding of the structure-activity relationships. This study suggests that hydroxamates may serve as a general scaffold for developing metal-mediated inhibitors against protein tyrosine kinases. To the best of our knowledge, this is the first report of designing metal-mediated inhibitors against a protein tyrosine kinase by targeting a metal binding site.

  DOI：

  10.1021/jm061058c
• 作为产物：
  描述：

  3-(4-甲氧基苯基)-2-苯基丙酸 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2R)-3-(4-hydroxyphenyl)-2-phenylpropanoic acid
  参考文献：
  名称：

  Deracemization of α-substituted arylacetic acids

  摘要：

  Reaction of rac-alpha-substituted arylacetyl chlorides with (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone under standard esterification conditions, gave esters (3R,alpha R)- and (3S,alpha S)-3, respectively, with a diastereoselectivity which diminishes on increasing the steric effect of the alpha-substituent. Controlled acidic hydrolysis of esters 3 afforded the corresponding acids 4 with minimal racemization. Boron tribromide demethylation of (R)- and (S)-4d gave without racemization the hydroxyacids (R)- and (S)-4e, known precursors of (R)- and (S)-iodoalphionic acid. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00129-2

文献信息

• Heterogeneous Enantioselective Hydrogenation of Hydroxy-substituted (E)-2,3-diphenylpropenoic Acids over Pd/Al2O3 Modified by Cinchonidine
  作者：György Szőllősi

  DOI：10.1007/s10562-012-0777-5

  日期：2012.3

  The enantioselective hydrogenation of (E)-2,3-diphenylpropenoic acids substituted by hydroxyl group has been studied over Pd/Al2O3 catalyst modified by cinchonidine. The effect of the acidic hydroxyl substituents was compared with that of the methoxy group in the same position. The para-hydroxyl substituent on the 3-phenyl ring had similar effect on the enantioselectivity as the methoxy group, whereas

  在辛可尼丁改性的Pd/Al2O3催化剂上研究了羟基取代的(E)-2,3-二苯基丙烯酸的对映选择性加氢。将酸性羟基取代基的影响与相同位置的甲氧基的影响进行比较。3-苯环上的对羟基取代基对对映选择性的影响与甲氧基相似，而间位取代了饱和酸的光学纯度。这是通过在这些位置存在电子释放取代基时获得的对映选择性增加的不同来源来解释的。尽管 2-苯环上的对羟基对单取代酸加氢的对映选择性有有益影响，在 3-苯环上存在氟或羟基时，两个取代基的影响不相加。该研究表明，辛可尼丁修饰的 Pd 催化剂适用于制备几种具有良好光学纯度的羟基取代的 2,3-二苯基丙酸，将该催化体系的范围扩展到新型多功能手性结构单元。Graphical AbstractHeterogeneous Enantioselective辛可尼定改性的 Pd/Al2O3 上羟基取代的 (E)-2,3-二苯基丙烯酸的氢化。
• Potent α4β1 Peptide Antagonists as Potential Anti-Inflammatory Agents
  作者：David Y. Jackson、Clifford Quan、Dean R. Artis、Thomas Rawson、Brent Blackburn、Martin Struble、Geraldine Fitzgerald、Kathryn Chan、Sheldon Mullins、J. P. Burnier、Wayne J. Fairbrother、Kevin Clark、Maureen Berisini、Henry Chui、Mark Renz、Susan Jones、Sherman Fong

  DOI：10.1021/jm970175s

  日期：1997.10.1

  migration, adhesion, and subsequent extravasation of leukocytes into inflamed tissues contribute to the pathogenesis of a variety of inflammatory diseases including asthma, rheumatoid arthritis, inflammatory bowel disease, and multiple sclerosis. The integrin adhesion receptor alpha 4 beta 1 expressed on leukocytes binds to the extracellular matrix protein fibronectin and to the cytokine inducible vascular

  白细胞向发炎组织的迁移，粘附和随后的外渗促成多种炎性疾病的发病机理，包括哮喘，类风湿性关节炎，炎性肠病和多发性硬化症。在白细胞上表达的整联蛋白粘附受体α4 beta 1在发炎部位与细胞外基质蛋白纤连蛋白和细胞因子诱导的血管细胞粘附分子-1（VCAM-1）结合。α4 beta 1与VCAM-1的结合可引发白细胞与血管内皮的牢固粘附，然后渗入组织。针对alpha 4 beta 1或VCAM-1产生的单克隆抗体可以在多种动物模型中缓解这种炎症反应。最近，含有基于纤连蛋白连接节段1（CS-1）的共有LDV序列的肽和含有RCD基序的环状肽已显示出有望通过阻断α4 beta 1与VCAM-的相互作用来调节白细胞迁移和炎症。 1。在这里，我们描述了新颖，高效的环状肽，它们在亚纳摩尔浓度下竞争性抑制α4β1与VCAM-1和纤连蛋白的结合。代表性类似物的结构通过NMR光谱法确定，并用于促进肽前导的优化。本文
• Design and Evaluation of Hydroxamate Derivatives as Metal-Mediated Inhibitors of a Protein Tyrosine Kinase
  作者：Xianfeng Gu、Yuehao Wang、Anil Kumar、Guofeng Ye、Keykavous Parang、Gongqin Sun

  DOI：10.1021/jm061058c

  日期：2006.12.1

  Protein tyrosine kinases use two Mg2+ ions as cofactors in catalysis, one as the ATP-Mg complex (M1) and the other as an essential activator (M2). The M2-binding site has high affinity for transition metal cations such as cobalt and zinc. Taking advantage of this high affinity, we examined hydroxamates as metal-mediated inhibitors against C-terminal Src kinase (Csk), a protein tyrosine kinase. Of a small group of amino acid hydroxamates, tyrosine and phenylalanine hydroxamates inhibited Csk activity only in the presence of Co2+. Four classes of phenylalanine and tyrosine hydroxamate derivatives were synthesized and evaluated as metal-mediated inhibitors of Csk, leading to improved inhibition and a better understanding of the structure-activity relationships. This study suggests that hydroxamates may serve as a general scaffold for developing metal-mediated inhibitors against protein tyrosine kinases. To the best of our knowledge, this is the first report of designing metal-mediated inhibitors against a protein tyrosine kinase by targeting a metal binding site.
• Deracemization of α-substituted arylacetic acids
  作者：Pelayo Camps、Sílvia Giménez

  DOI：10.1016/0957-4166(96)00129-2

  日期：1996.4

  Reaction of rac-alpha-substituted arylacetyl chlorides with (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone under standard esterification conditions, gave esters (3R,alpha R)- and (3S,alpha S)-3, respectively, with a diastereoselectivity which diminishes on increasing the steric effect of the alpha-substituent. Controlled acidic hydrolysis of esters 3 afforded the corresponding acids 4 with minimal racemization. Boron tribromide demethylation of (R)- and (S)-4d gave without racemization the hydroxyacids (R)- and (S)-4e, known precursors of (R)- and (S)-iodoalphionic acid. Copyright (C) 1996 Elsevier Science Ltd