(S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid isopropyl ester | 325793-71-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid isopropyl ester
• 英文别名: 2-ethoxy-3-(4-hydroxyphenyl)propionic acid isopropyl ester；isopropyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate；isopropyl (S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate；isopropyl (S)-2-ethoxy-3-(4-hydroxyphenyl)propionate；isopropyl (S)-3-(4-hydroxyphenyl)-2-ethoxypropionate；(S)-2-propyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate；propan-2-yl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate
• CAS: 325793-71-3
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: XRWDRCMXDCLIOS-ZDUSSCGKSA-N

物化性质

• 沸点：
  374.9±27.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid isopropyl ester 在 sodium hydroxide 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 36.0h， 生成 ragaglitazar
  参考文献：
  名称：

  Synthesis and Biological and Structural Characterization of the Dual-Acting Peroxisome Proliferator-Activated Receptor α/γ Agonist Ragaglitazar

  摘要：

  A new and improved synthesis of the peroxisome proliferator-activated receptor (PPAR) agonist ragaglitazar applicable for large-scale preparation has been developed. The convergent synthetic procedure was based on a novel enzymatic kinetic resolution step. The conformation of ragaglitazar bound to the hPPARgamma receptor was quite different compared to the single-crystal structures of the L-arginine salt of ragaglitazar. In particular, the phenoxazine ring system had varying orientations. Ragaglitazar had high affinity for the hPPARalpha and -gamma receptors with IC50 values of 0.98 and 0.092 muM, respectively. The lack of hPPARdelta activity could be explained by the absence of binding in the tail-up pocket in the hPPARdelta receptor, in contrast to the hPPARdelta agonist GW2433, which was able to bind in both the tail-up and tail-down pockets of the receptor.

  DOI：

  10.1021/jm021027r
• 作为产物：
  描述：

  4-苄氧基苯甲醛 在 palladium on activated charcoal 氯化亚砜 、 phosphate buffer 、 Pectinex Ultra SP-L enzyme 、 potassium tert-butylate 、 氢气 作用下， 以 叔丁醇 为溶剂， 反应 46.5h， 生成 (S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid isopropyl ester
  参考文献：
  名称：

  Synthesis and Biological and Structural Characterization of the Dual-Acting Peroxisome Proliferator-Activated Receptor α/γ Agonist Ragaglitazar

  摘要：

  A new and improved synthesis of the peroxisome proliferator-activated receptor (PPAR) agonist ragaglitazar applicable for large-scale preparation has been developed. The convergent synthetic procedure was based on a novel enzymatic kinetic resolution step. The conformation of ragaglitazar bound to the hPPARgamma receptor was quite different compared to the single-crystal structures of the L-arginine salt of ragaglitazar. In particular, the phenoxazine ring system had varying orientations. Ragaglitazar had high affinity for the hPPARalpha and -gamma receptors with IC50 values of 0.98 and 0.092 muM, respectively. The lack of hPPARdelta activity could be explained by the absence of binding in the tail-up pocket in the hPPARdelta receptor, in contrast to the hPPARdelta agonist GW2433, which was able to bind in both the tail-up and tail-down pockets of the receptor.

  DOI：

  10.1021/jm021027r
• 作为试剂：
  描述：

  (S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid isopropyl ester 、 2-(10H-Phenoxazin-10-yl)ethyl methanesulfonate 在 (S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid isopropyl ester 作用下， 生成 (S)-2-propyl 2-ethoxy-3-(4-[2-(phenoxazine-10-yl)ethoxy]phenyl)propanoate
  参考文献：
  名称：

  J. Label. Compd. Radiopharm. 2003, 46, 475-488

  摘要：

  DOI：

文献信息

• [EN] DICARBOXYLIC ACID DERIVATIVES AS PPAR-AGONISTS<br/>[FR] DERIVES D'ACIDE DICARBOXYLIQUE EN TANT QU'AGONISTES PPAR
  申请人：NOVO NORDISK AS

  公开号：WO2004056740A1

  公开（公告）日：2004-07-08

  A novel class of dicarboxylic acid derivatives, the use of these compounds as phar-maceutical compositions, pharmaceutical compositions comprising the compounds and meth-ods of treatment employing these compounds and compositions. The present compounds may be useful in the treatment and/or prevention of conditions mediated by Peroxisome Prolifera-tor-Activated Receptors (PPAR).

  一种新型的二元酸衍生物，这些化合物的用途作为药物组合物，包含这些化合物的药物组合物以及使用这些化合物和组合物进行治疗的方法。本发明的化合物可能用于治疗和/或预防由过氧化物酶体增殖物激活受体（PPAR）介导的条件。
• Novel compounds, their preparation and use
  申请人：——

  公开号：US20040259950A1

  公开（公告）日：2004-12-23

  A novel class of dicarboxylic acid derivatives, the use of these compounds as pharmaceutical compositions, pharmaceutical compositions comprising the compounds and methods of treatment employing these compounds and compositions. The present compounds may be useful in the treatment and/or prevention of conditions mediated by Peroxisome Proliferator-Activated Receptors (PPAR).

  一种新型的二羧酸衍生物类，这些化合物作为药物组成物的用途，包括这些化合物的药物组成物和使用这些化合物和组成物进行治疗的方法。这些化合物可能在治疗和/或预防由过氧化物酶体增殖物激活受体（PPAR）介导的疾病方面有用。
• [EN] AMIDE LINKER PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR MODULATORS<br/>[FR] MODULATEURS DE RECEPTEUR ACTIVE DE LA PROLIFERATION DES PEROXISOMES A LIEUR AMIDE
  申请人：LILLY CO ELI

  公开号：WO2004000789A1

  公开（公告）日：2003-12-31

  The present invention is directed to compounds, compositions, and use of compounds the structural Formula (I).

  本发明涉及结构式(I)的化合物、组合物及其使用。
• Synthesis of PPAR Agonist via Asymmetric Hydrogenation of a Cinnamic Acid Derivative and Stereospecific Displacement of (<i>S</i>)-2-Chloropropionic Acid
  作者：Ioannis N. Houpis、Lawrence E. Patterson、Charles A. Alt、John R. Rizzo、Tony Y. Zhang、Michael Haurez

  DOI：10.1021/ol050367e

  日期：2005.5.1

  synthesis of the peroxime proliferator activated receptor (PPAR) alpha,gamma-agonist (1) was accomplished with high enantio- and diastereoselectivity by employing an asymmetric hydrogenation strategy, of an alpha-alkoxy cinnamic acid derivative, to set the C-2 chiral center. A diastereospecific S(N)2 displacement under mild basic conditions established the C-10 stereochemistry without any detectable racemization

  过氧化物酶增殖物激活受体（PPAR）α，γ-激动剂（1）的合成通过采用α-烷氧基肉桂酸衍生物的不对称氢化策略设定C-2手性以高对映异构和非对映选择性完成中央。在温和的碱性条件下，非对映体特异性S（N）2取代建立了C-10立体化学，而没有两个可差向异构手性中心的可检测消旋作用。
• [EN] A PROCESS FOR THE PREPARATION OF 3-ARYL-2-HYDROXY PROPANOIC ACID COMPOUNDS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS D'ACIDE PROPANOÏQUE 3-ARYL-2-HYDROXY
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2014181362A1

  公开（公告）日：2014-11-13

  The present disclosure provides a process for synthesis of 3-aryl-2-hydroxy propanoic acid derivatives of formula (S)-1. wherein R1 represents H or (C1-C5) alkyl groups and R2 represents (C1-C5) alkyl groups.

  本公开提供了一种合成式（S）-1的3-芳基-2-羟基丙酸衍生物的过程。其中R1代表H或（C1-C5）烷基基团，R2代表（C1-C5）烷基基团。