Ethyl 2-[4-(bromomethyl)phenoxy]-3-phenylpropanoate | 1191933-79-5

• 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: Ethyl 2-[4-(bromomethyl)phenoxy]-3-phenylpropanoate
• CAS: 1191933-79-5
• 化学式: C₁₈H₁₉BrO₃
• 分子量: 363.251
• InChiKey: OEMAKOKWNSQZHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 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-(bromomethyl)phenoxy]-3-phenylpropanoate 、 苯硫酚 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以47%的产率得到ethyl 2-(4-phenylthiomethyl-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
• 作为产物：
  描述：

  ethyl 2-(4-hydroxymethyl-phenoxy)-3-phenyl-propanoate 在 三溴化磷 作用下， 以66%的产率得到Ethyl 2-[4-(bromomethyl)phenoxy]-3-phenylpropanoate
  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

文献信息

• 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
  作者：Giuseppe Fracchiolla、Antonio Laghezza、Luca Piemontese、Paolo Tortorella、Fernando Mazza、Roberta Montanari、Giorgio Pochetti、Antonio Lavecchia、Ettore Novellino、Sabata Pierno、Diana Conte Camerino、Fulvio Loiodice

  DOI：10.1021/jm900941b

  日期：2009.10.22

  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.