(S)-3-(4-benzyloxyphenyl)-2-(4-chlorophenoxy)propionic acid | 710327-33-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3-(4-benzyloxyphenyl)-2-(4-chlorophenoxy)propionic acid
• CAS: 710327-33-6
• 化学式: C₂₂H₁₉ClO₄
• 分子量: 382.843
• InChiKey: AAKJWVKAFUXEOD-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-benzyloxyphenyl)-2-(4-chlorophenoxy)propionic acid 在 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 乙醇 为溶剂， 生成 ethyl (S)-2-(4-chlorophenoxy)-3-(4-hydroxyphenyl)propionate
  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：

  ethyl 3-(4-benzyloxyphenyl)lactate 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， 生成 (S)-3-(4-benzyloxyphenyl)-2-(4-chlorophenoxy)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

文献信息

• Synthesis and biological activity of novel α-substituted β-phenylpropionic acids having pyridin-2-ylphenyl moiety as antihyperglycemic agents
  作者：Makoto Takamura、Mitsuya Sakurai、Eriko Yamada、Sachie Fujita、Makoto Yachi、Toshiyuki Takagi、Aya Isobe、Yuka Hagisawa、Toshihiko Fujiwara、Hiroaki Yanagisawa

  DOI：10.1016/j.bmc.2004.01.048

  日期：2004.5

  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.