ethyl 2-(4-cis-styryl-phenoxy)-3-phenyl-propanoate | 1191933-92-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: ethyl 2-(4-cis-styryl-phenoxy)-3-phenyl-propanoate
• 英文别名: ethyl 3-phenyl-2-[4-[(Z)-2-phenylethenyl]phenoxy]propanoate
• CAS: 1191933-92-2
• 化学式: C₂₅H₂₄O₃
• 分子量: 372.464
• InChiKey: WWXNVYQVZHWLRW-YPKPFQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-cis-styryl-phenoxy)-3-phenyl-propanoate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-(4-cis-styryl-phenoxy)-3-phenyl-propanoic acid
  参考文献：
  名称：

  New 2-Aryloxy-3-phenyl-propanoic Acids As Peroxisome Proliferator-Activated Receptors α/γ Dual Agonists with Improved Potency and Reduced Adverse Effects on Skeletal Muscle Function

  摘要：

  The preparation of a new series of 2-aryloxy-3-phenyl-propanoic acids, resulting from the introduction of a linker into the diphenyl system of the previously reported PPAR alpha/gamma dual agonist 1, allowed the identification of new ligands with improved potency on PPAR alpha and unchanged activity on PPAR gamma. For the most interesting stereoisomers S-2 and S-4, X-ray studies in PPAR gamma and docking experiments in PPAR alpha provided a molecular explanation for their different behavior as full and partial agonists of PPAR alpha and PPAR gamma, respectively. Due to the adverse effects provoked by hypolipidemic drugs on skeletal muscle function, we also investigated the blocking activity of S-2 and S-4 on skeletal muscle membrane chloride channel conductance and found that these ligands have a pharmacological profile more beneficial compared to fibrates currently used in therapy.

  DOI：

  10.1021/jm900941b
• 作为产物：
  描述：

  ethyl 2-(4-formylphenoxy)-3-phenylpropanoate 、 苄基三苯基氯化膦 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 5.5h， 以19%的产率得到ethyl 2-(4-cis-styryl-phenoxy)-3-phenyl-propanoate
  参考文献：
  名称：

  New 2-Aryloxy-3-phenyl-propanoic Acids As Peroxisome Proliferator-Activated Receptors α/γ Dual Agonists with Improved Potency and Reduced Adverse Effects on Skeletal Muscle Function

  摘要：

  The preparation of a new series of 2-aryloxy-3-phenyl-propanoic acids, resulting from the introduction of a linker into the diphenyl system of the previously reported PPAR alpha/gamma dual agonist 1, allowed the identification of new ligands with improved potency on PPAR alpha and unchanged activity on PPAR gamma. For the most interesting stereoisomers S-2 and S-4, X-ray studies in PPAR gamma and docking experiments in PPAR alpha provided a molecular explanation for their different behavior as full and partial agonists of PPAR alpha and PPAR gamma, respectively. Due to the adverse effects provoked by hypolipidemic drugs on skeletal muscle function, we also investigated the blocking activity of S-2 and S-4 on skeletal muscle membrane chloride channel conductance and found that these ligands have a pharmacological profile more beneficial compared to fibrates currently used in therapy.

  DOI：

  10.1021/jm900941b