ethyl (S)-2-ethoxy-3-(3-hydroxyphenyl)propanoate | 1072031-80-1

• 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: ethyl (S)-2-ethoxy-3-(3-hydroxyphenyl)propanoate
• 英文别名: ethyl (2S)-2-ethoxy-3-(3-hydroxyphenyl)propanoate
• CAS: 1072031-80-1
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: YVPGIROMVYUBPE-LBPRGKRZSA-N

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

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 ethyl (S)-2-ethoxy-3-(3-hydroxyphenyl)propanoate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Novel Constrained meta-Substituted Phenyl Propanoic Acids as Peroxisome Proliferator-Activated Receptor α and γ Dual Agonists

  摘要：

  In an effort to develop dual PPAR alpha/gamma activators with improved therapeutic efficacy, a series of diaryl alpha-ethoxy propanoic acid compounds comprising two aryl groups linked by rigid oxime ether or isoxazoline ring were designed and synthesized and their biological activities were examined. Most of the compounds possessing an oxime ether linker were more potent PPAR gamma activators than the lead PPAR alpha/gamma dual agonist, tesaglitazar in vitro. Compound 18, one of the derivatives with an oxime ether linker, was found to selectively transactivate PPAR gamma (EC(50) = 0.028 mu M) over PPAR alpha (EC(50) = 7.22 mu M) in vitro and lower blood glucose in db/db mice more than muraglitazar after oral treatment for 11 days.

  DOI：

  10.1021/jm8003416
• 作为产物：
  描述：

  ethyl (2S)-3-(3-acetyloxyphenyl)-2-ethoxypropanoate 在 三甲基氯硅烷 作用下， 以 乙醇 为溶剂， 以81%的产率得到ethyl (S)-2-ethoxy-3-(3-hydroxyphenyl)propanoate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Novel Constrained meta-Substituted Phenyl Propanoic Acids as Peroxisome Proliferator-Activated Receptor α and γ Dual Agonists

  摘要：

  In an effort to develop dual PPAR alpha/gamma activators with improved therapeutic efficacy, a series of diaryl alpha-ethoxy propanoic acid compounds comprising two aryl groups linked by rigid oxime ether or isoxazoline ring were designed and synthesized and their biological activities were examined. Most of the compounds possessing an oxime ether linker were more potent PPAR gamma activators than the lead PPAR alpha/gamma dual agonist, tesaglitazar in vitro. Compound 18, one of the derivatives with an oxime ether linker, was found to selectively transactivate PPAR gamma (EC(50) = 0.028 mu M) over PPAR alpha (EC(50) = 7.22 mu M) in vitro and lower blood glucose in db/db mice more than muraglitazar after oral treatment for 11 days.

  DOI：

  10.1021/jm8003416

文献信息

• New compounds, their preparation and use
  申请人：——

  公开号：US20010041709A1

  公开（公告）日：2001-11-15

  The present invention relates to compounds of formula (I) 1 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）。
• Combination therapy using a dual PPAR-a/PPAR-y activator and a GLP-1 derivative for the treatment of metabolic syndrome and related diseases and disorders
  申请人：——

  公开号：US20030199451A1

  公开（公告）日：2003-10-23

  The present invention relates to a pharmaceutical composition comprising a dual Peroxisome Proliferator-Activated Receptor-alpha/Peroxisome Proliferator-Activated Receptor-gama activator (PPAR-&agr;/PPAR-&ggr;) and a Glucagon Like Peptide-1 (GLP-1) derivative for treating, preventing and reducing the risk of developing Type 2 diabetes, insulin resistance, dyslipidemia, obesity, hypertension and other related diseases and disorders.

  本发明涉及一种药物组成物，包括一个双过氧化物酶体增殖物激活受体-α/过氧化物酶体增殖物激活受体-γ激活剂（PPAR-α/PPAR-γ）和一种胰高血糖素样肽-1（GLP-1）衍生物，用于治疗、预防和降低发展2型糖尿病、胰岛素抵抗、血脂异常、肥胖症、高血压和其他相关疾病和障碍的风险。
• US6569901B2
  申请人：——

  公开号：US6569901B2

  公开（公告）日：2003-05-27
• US7202213B2
  申请人：——

  公开号：US7202213B2

  公开（公告）日：2007-04-10
• Design, Synthesis, and Biological Evaluation of Novel Constrained <i>meta</i>-Substituted Phenyl Propanoic Acids as Peroxisome Proliferator-Activated Receptor α and γ Dual Agonists
  作者：Young-Ger Suh、Nam-Jung Kim、Bon-Woong Koo、Kwang-Ok Lee、Sung-Hyun Moon、Dong-Hyung Shin、Jong-Wha Jung、Seung-Mann Paek、Dong-Jo Chang、Funan Li、Hyun-Jin Kang、Tuong Vy Thi Le、Yu Na Chae、Chang Yell Shin、Mi-Kyung Kim、Joong In Lim、Jae-Sang Ryu、Hyun-Ju Park

  DOI：10.1021/jm8003416

  日期：2008.10.23

  In an effort to develop dual PPAR alpha/gamma activators with improved therapeutic efficacy, a series of diaryl alpha-ethoxy propanoic acid compounds comprising two aryl groups linked by rigid oxime ether or isoxazoline ring were designed and synthesized and their biological activities were examined. Most of the compounds possessing an oxime ether linker were more potent PPAR gamma activators than the lead PPAR alpha/gamma dual agonist, tesaglitazar in vitro. Compound 18, one of the derivatives with an oxime ether linker, was found to selectively transactivate PPAR gamma (EC(50) = 0.028 mu M) over PPAR alpha (EC(50) = 7.22 mu M) in vitro and lower blood glucose in db/db mice more than muraglitazar after oral treatment for 11 days.