(S)-2-(4'-isopropylphenyl) propionic acid | 95976-43-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-2-(4'-isopropylphenyl) propionic acid
• 英文别名: (2S)-2-(4-propan-2-ylphenyl)propanoic acid
• CAS: 95976-43-5
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: DESVPZPAXGJCGM-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(4'-isopropylphenyl) propionic acid 在 palladium on activated charcoal 二苯基膦叠氮化物 、 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 18.75h， 生成 (αs)-α-甲基-4-(1-甲基乙基)-苯甲胺
  参考文献：
  名称：

  Phosphotyrosine-Containing Dipeptides as High-Affinity Ligands for the p56^lck SH2 Domain

  摘要：

  Src homology-2 (SH2) domains are noncatalytic motifs containing approximately 100 amino acid residues that are involved in intracellular signal transduction. The phosphotyrosine-containing tetrapeptide Ac-pYEEI binds to the SH2 domain of p.56(lck) (Lck) with an affinity of 0.1 mu M. Starting from Ac-pYEEI, we have designed potent antagonists of the Lck SH2 domain which are reduced in peptidic character and in which the three carboxyl groups have been eliminated. The two C-terminal amino acids (EI) have been replaced by benzylamine derivatives and the pY + 1 glutamic acid has been substituted with leucine. The best C-terminal fragment identified, (S)-1-(4-isopropylphenyl)ethylamine, binds to the Lck SH2 domain better than the C-terminal dipeptide EI. Molecular modeling suggests that the substituents at the 4-position of the phenyl ring occupy the pY + 3 lipophilic pocket in the SH2 domain originally occupied by the isoleucine side chain. This new series of phosphotyrosine-containing dipeptides binds to the Lck SH2 domain with potencies comparable to that of tetrapeptide 1.

  DOI：

  10.1021/jm980612i
• 作为产物：
  描述：

  4-isopropylphenylacetyl chloride 在 lithium hydroxide 、 正丁基锂 、 双氧水 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 (S)-2-(4'-isopropylphenyl) propionic acid
  参考文献：
  名称：

  Phosphotyrosine-Containing Dipeptides as High-Affinity Ligands for the p56^lck SH2 Domain

  摘要：

  Src homology-2 (SH2) domains are noncatalytic motifs containing approximately 100 amino acid residues that are involved in intracellular signal transduction. The phosphotyrosine-containing tetrapeptide Ac-pYEEI binds to the SH2 domain of p.56(lck) (Lck) with an affinity of 0.1 mu M. Starting from Ac-pYEEI, we have designed potent antagonists of the Lck SH2 domain which are reduced in peptidic character and in which the three carboxyl groups have been eliminated. The two C-terminal amino acids (EI) have been replaced by benzylamine derivatives and the pY + 1 glutamic acid has been substituted with leucine. The best C-terminal fragment identified, (S)-1-(4-isopropylphenyl)ethylamine, binds to the Lck SH2 domain better than the C-terminal dipeptide EI. Molecular modeling suggests that the substituents at the 4-position of the phenyl ring occupy the pY + 3 lipophilic pocket in the SH2 domain originally occupied by the isoleucine side chain. This new series of phosphotyrosine-containing dipeptides binds to the Lck SH2 domain with potencies comparable to that of tetrapeptide 1.

  DOI：

  10.1021/jm980612i

文献信息

• Chemoenzymatic synthesis of pure enantiomeric 2-aryl propionic acids.
  作者：Mariano García、Carmen del Campo、Emilio F. lama、José M. Sánchez-Montero、José V. Sinisterra

  DOI：10.1016/s0040-4020(01)81926-8

  日期：1993.1

  A new chemoenzymatic procedure to obtain pure enantiomeric 2-arylpropionic acids is described. The one pot synthesis of (±)-2-arylpropionic acids is carried out by addition of dichlorocarbene to the O bond of arylmethylketones and hydrogenolysis of the addition product. The racemic mixture is resolved by enantiospecific hydrolysis of the racemic ethyl esters using native lipase from Candida rugosa

  描述了一种获得纯对映体2-芳基丙酸的新化学酶法。一锅合成（±）-2-芳基丙酸是通过将二氯卡宾加成至芳基甲基酮的O键并加成产物进行氢解来进行的。外消旋混合物通过使用来自假丝酵母的天然脂肪酶的外消旋乙酯的对映体特异性水解来拆分。良好的收率，起始的芳基甲基酮的可及性和酶促水解的立体特异性使该方法变得有趣，以便获得相同的非甾体类抗炎药，如布洛芬或萘普生。
• Compounds co-inducing cholinergic up-regulation and inflammation down-regulation and uses thereof
  申请人：Israel Institute for Biological Research

  公开号：US20020160988A1

  公开（公告）日：2002-10-31

  Chimeric compounds are disclosed which are covalent conjugates of reversible or irreversible cholinergic up-regulators and non-steroidal anti-inflammatory drugs (NSAIDs), methods for their synthesis and use thereof for treatment and/or prevention of central nervous system (CNS) disorders and diseases.

  本发明揭示了嵌合化合物，它们是可逆或不可逆胆碱能上调剂和非甾体抗炎药（NSAIDs）的共价结合物，以及用于合成它们和用于治疗和/或预防中枢神经系统（CNS）疾病和疾病的方法。
• EP1385824A2
  申请人：——

  公开号：EP1385824A2

  公开（公告）日：2004-02-04
• Amphiphilic pyridinium compounds, method of making and use thereof
  申请人：Pollard B. Harvey

  公开号：US20070105916A1

  公开（公告）日：2007-05-10

  The present invention is directed to the amphiphilic pyridinium compounds, such as for suppressing IL-8 secretion and production. The present invention further provides methods of making and using such compounds for the treatment of the IL-8 related diseases, such as cystic fibrosis.
• US7893094B2
  申请人：——

  公开号：US7893094B2

  公开（公告）日：2011-02-22