ethyl 3-(4-hydroxyphenyl)-2-phenylthiopropionate | 710326-88-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 3-(4-hydroxyphenyl)-2-phenylthiopropionate
• 英文别名: 3-(4-Hydroxyphenyl)-2-phenylsulfanylpropanoic acid ethyl ester；ethyl 3-(4-hydroxyphenyl)-2-phenylsulfanylpropanoate
• CAS: 710326-88-8
• 化学式: C₁₇H₁₈O₃S
• 分子量: 302.394
• InChiKey: NPVWEYPOWKARNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-(4-hydroxyphenyl)-2-phenylthiopropionate 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 33.0h， 生成 2-Phenylsulfanyl-3-(4-{2-[1-(4-pyridin-2-yl-phenyl)-eth-(E)-ylideneaminooxy]-ethoxy}-phenyl)-propionic acid
  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
• 作为产物：
  描述：

  3-(4-羟基苯基)乳酸乙酯 在 盐酸 、 18-冠醚-6 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.5h， 生成 ethyl 3-(4-hydroxyphenyl)-2-phenylthiopropionate
  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

文献信息

• [EN] NEW 3-ARYL PROPIONIC ACID DERIVATIVES AND ANALOGS<br/>[FR] NOUVEAUX DERIVES D'ACIDE 3-ARYL PROPIONIQUE ET ANALOGUES
  申请人：ASTRAZENECA AB

  公开号：WO1999062871A1

  公开（公告）日：1999-12-09

  (EN) Novel 3-aryl proprionic acid derivatives and analogs, having general formula (I) and stereo- and optical isomers and racemates thereof as well as pharmaceutically acceptable salts, solvates and crystalline forms thereof, process for their manufacture, pharmaceutical preparations containing them and the use of the compounds in clinical conditions associated with insulin resistance.(FR) L'invention concerne de nouveaux dérivés d'acide 3-aryl-propionique et leurs analogues, ayant la formule générale (I). L'invention concerne également leurs stéréo-isomères, leurs isomères optiques, leurs racémates ainsi que leurs sels pharmaceutiquement acceptables, leurs solvates et leurs formes cristallines. L'invention concerne enfin leur procédé de production, les préparations pharmaceutiques les contenant et l'utilisation de ces composés dans des états cliniques associés une insulinorésistance.

  (中) 新型3-芳基丙酸衍生物及其类似物，具有通式（I）和其立体和光学异构体以及它们的盐，溶剂化合物和晶体形式，其制造方法，包含它们的制药制剂以及在与胰岛素抵抗有关的临床情况下使用这些化合物的用途。
• New 3-aryl propionic acid derivatives and analogs
  申请人：——

  公开号：US20040229949A1

  公开（公告）日：2004-11-18

  Novel 3-aryl propionic acid derivatives and analogs, process and intermediate for their manufacture, pharmaceutical preparations containing them and the use of the compounds in clinical conditions associated with insulin resistance.

  小说3-芳基丙酸衍生物和类似物，其制造过程和中间体，含有它们的制药制剂以及在与胰岛素抵抗相关的临床病症中使用这些化合物的用途。
• 3-aryl propionic acid derivatives and analogs
  申请人：AstraZeneca AB

  公开号：US06630600B1

  公开（公告）日：2003-10-07

  Novel 3-aryl propionic acid derivatives and analogs, process and intermediate for their manufacture, pharmaceutical preparations containing them and the use of the compounds in clinical conditions associated with insulin resistance.

  小说3-芳基丙酸衍生物和类似物，其制造过程和中间体，含有它们的制药制剂以及在与胰岛素抵抗相关的临床情况中使用化合物的用途。
• NEW 3-ARYL PROPIONIC ACID DERIVATIVES AND ANALOGS
  申请人：AstraZeneca AB

  公开号：EP1084102A1

  公开（公告）日：2001-03-21
• US6630600B1
  申请人：——

  公开号：US6630600B1

  公开（公告）日：2003-10-07