ethyl 2-hydroxy-3-[4-(methoxymethoxy)phenyl]propionate | 710326-87-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 2-hydroxy-3-[4-(methoxymethoxy)phenyl]propionate
• CAS: 710326-87-7
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: WWDIQYSBAYTPPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-hydroxy-3-[4-(methoxymethoxy)phenyl]propionate 在 盐酸 、 sodium hydroxide 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 35.5h， 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：

  氯甲基甲基醚 、 3-(4-羟基苯基)乳酸乙酯 在 18-冠醚-6 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.0h， 以29%的产率得到ethyl 2-hydroxy-3-[4-(methoxymethoxy)phenyl]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