2-乙氧基-3-对羟基苯基丙酸乙酯 | 197299-16-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-乙氧基-3-对羟基苯基丙酸乙酯
• 中文别名: 3-(4-羟基苯基)-2-乙氧基丙酸乙酯
• 英文名称: ethyl 2-ethoxy-3-(4-hydroxy-phenyl)-propionate
• 英文别名: ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate
• CAS: 197299-16-4
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: NEJJCKFYYBEQRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  367.3±27.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  2-乙氧基-3-对羟基苯基丙酸乙酯 在 sodium hydroxide 、 氯化亚砜 、 phosphate buffer 、 Pectinex Ultra SP-L enzyme 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 82.0h， 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：

  ethyl 3-(4-benzyloxyphenyl)lactate 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.0h， 生成 2-乙氧基-3-对羟基苯基丙酸乙酯
  参考文献：
  名称：

  Synthesis and biological activity of novel α-substituted β-phenylpropionic acids having pyridin-2-ylphenyl moiety as antihyperglycemic agents

  摘要：

  We previously reported the identification of novel oximes having 5-benzyl-2,4-thiazolidinedione with anti hyperglycemic activity. We now report the synthesis and biological activity of a novel series of oximes and amides having alpha-substituted-beta-phenylpropionic acids. In this series, we obtained potent PPARalpha/gamma dual agonist (S)-9d, with which activation of PPARalpha and PPARgamma was considerably more potent than that of the reference compounds GW9578 22 and rosiglitazone 3, respectively. This means (S)-9d is of the strongest class of PPARalpha/gamma dual agonists. In the course of this study, we also obtained 8h, which indicated potent plasma glucose lowering effect in spite of weak PPARalpha/gamma agonistic activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.048
• 作为试剂：
  描述：

  ethyl 3-(4-benzyloxyphenyl)-2-ethoxypropionate 、 氢气 在 钯 2-乙氧基-3-对羟基苯基丙酸乙酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以to afford the title compound of the formula (13a) (28-29 g, 97-98%)的产率得到2-乙氧基-3-对羟基苯基丙酸乙酯
  参考文献：
  名称：

  Process for the preparation of new antidiabetic agents

  摘要：

  本发明涉及一种改进的制备新型抗糖尿病化合物的过程，其化学式为（1），其中R1代表氢或低碳基团，X代表氢或卤素原子。

  公开号：

  US06531596B1

文献信息

• Design, synthesis, and structure–activity relationship of carbamate-tethered aryl propanoic acids as novel PPARα/γ dual agonists
  作者：Nam-Jung Kim、Kwang-Ok Lee、Bon-Woong Koo、Funan Li、Ja-Kyung Yoo、Hyun-Ju Park、Kyung-Hoon Min、Joong In Lim、Mi Kyung Kim、Jin-Kwan Kim、Young-Ger Suh

  DOI：10.1016/j.bmcl.2007.04.057

  日期：2007.7

  dual agonists, which show excellent agonistic activity in PPARalpha/gamma transactivation assay. In particular, (R)-9d was identified as a potent PPARalpha/gamma dual agonist with EC(50)s of 0.377 microM in PPARalpha and 0.136 microM in PPARgamma, respectively. Interestingly, the structure-activity relationship revealed that the stereochemistry of the identified PPARalpha/gamma dual agonists significantly

  我们开发了新型的PPARalpha /γ双激动剂，在PPARalpha /γ反式激活试验中显示出极好的激动活性。特别地，（R）-9d被确定为有效的PPARalpha /γ双重激动剂，其EC（50）在PPARalpha中为0.377 microM，在PPARgamma中为0.136 microM。有趣的是，结构-活性关系揭示了所鉴定的PPARα/γ双重激动剂的立体化学显着影响它们在PPARα中的激动活性，而不是在PPARγ中。
• [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。
• Compounds, their preparation and use
  申请人：Novo Nordisk A/S

  公开号：US06555577B1

  公开（公告）日：2003-04-29

  The present invention relates to compounds of the general formula (I) The compounds are useful in the treatment and/or prevention of conditions mediated by nuclear receptors, in particular the Peroxisome Proliferator-Activated Receptors (PPAR).

  本发明涉及一般式(I)的化合物。 这些化合物在治疗和/或预防由核受体介导的疾病中具有用途，特别是过氧化物酶体增殖激活受体（PPAR）。
• NOVEL PHENYLPROPIONIC ACID DERIVATIVES AS PEROXISOME PROLIFERATOR-ACTIVATED GAMMA RECEPTOR MODULATORS, METHOD OF THE SAME, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
  申请人：Moon Ho-Sang

  公开号：US20100063041A1

  公开（公告）日：2010-03-11

  The present invention provides a novel phenylpropionic acid derivative and a PPAR-γ modulator comprising the same as an active ingredient. The phenylpropionic acid derivative of the present invention has modulatory action on function of PPAR-γ and then exhibits hypoglycemic, hypolipidemic and insulin resistance-reducing effects on PPAR-mediated diseases or disorders. Therefore, the present invention is prophylactically or therapeutically effective for diabetes and metabolic diseases.

  本发明提供了一种新型苯丙酸衍生物，以及包含该衍生物作为活性成分的PPAR-γ调节剂。本发明的苯丙酸衍生物对PPAR-γ的功能具有调节作用，从而在PPAR介导的疾病或紊乱中表现出降糖、降脂和减少胰岛素抵抗的效果。因此，本发明在预防或治疗糖尿病和代谢性疾病方面具有预防或治疗效果。
• 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。