2-Ethoxy-3-[3-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)phenyl]propanoic acid | 1033781-54-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-Ethoxy-3-[3-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)phenyl]propanoic acid
• CAS: 1033781-54-2
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: DDXOKUHUAQEPLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Ethoxy-3-[3-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)phenyl]propanoic acid 、 D-苯甘氨醇 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以39%的产率得到(S)-3-(3-(5-phenyl-4,5-dihydroisoxazole-3-yl)phenyl)-2-ethoxy-N-((S)-2-hydroxy-1-phenylethyl)propanamide
  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 2-ethoxy-3-(3-(5-phenyl-4,5-dihydroisoxazole-3-yl)phenyl)propanoate 在 甲醇 、 lithium hydroxide monohydrate 、 水 作用下， 以 四氢呋喃 为溶剂， 生成 2-Ethoxy-3-[3-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)phenyl]propanoic acid
  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

• 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.