(-)-(S)-2-(4-chlorophenoxy)-3-[4-(trifluoromethyl)phenyl]propanoic acid | 1093231-47-0

• 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: (-)-(S)-2-(4-chlorophenoxy)-3-[4-(trifluoromethyl)phenyl]propanoic acid
• 英文别名: (S)-2-(4-chlorophenoxy)-3-(4-(trifluoromethyl)phenyl)propanoic acid；(2S)-2-(4-chlorophenoxy)-3-[4-(trifluoromethyl)phenyl]propanoic acid
• CAS: 1093231-47-0
• 化学式: C₁₆H₁₂ClF₃O₃
• 分子量: 344.718
• InChiKey: GKKPZUKGEAWMMS-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (-)-(S)-2-(4-chlorophenoxy)-3-[4-(trifluoromethyl)phenyl]propanoic acid 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular modeling investigation of chiral 2-(4-chloro-phenoxy)-3-phenyl-propanoic acid derivatives with PPARα and PPARγ agonist activity

  摘要：

  PPARs are ligand-activated transcription factors that govern lipid and glucose homeostasis and play a central role in cardiovascular disease, obesity, and diabetes. Herein, we present screening results for a series of chiral 2-(4-chloro-phenoxy)-3-phenyl-propanoic acid derivatives, some of which are potent PPAR gamma agonists as well as PPAR alpha agonists. To investigate the binding modes of the most interesting derivatives into the PPARa and PPAR gamma binding clefts and evaluate their agonist activity, docking experiments, molecular dynamics simulations, and MM-PBSA analysis were performed. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.09.045
• 作为产物：
  描述：

  ethyl (S)-2-(4-chlorophenoxy)-3-[4-(trifluoromethyl)phenyl]propanoate 在 sodium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到(-)-(S)-2-(4-chlorophenoxy)-3-[4-(trifluoromethyl)phenyl]propanoic acid
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular modeling investigation of chiral 2-(4-chloro-phenoxy)-3-phenyl-propanoic acid derivatives with PPARα and PPARγ agonist activity

  摘要：

  PPARs are ligand-activated transcription factors that govern lipid and glucose homeostasis and play a central role in cardiovascular disease, obesity, and diabetes. Herein, we present screening results for a series of chiral 2-(4-chloro-phenoxy)-3-phenyl-propanoic acid derivatives, some of which are potent PPAR gamma agonists as well as PPAR alpha agonists. To investigate the binding modes of the most interesting derivatives into the PPARa and PPAR gamma binding clefts and evaluate their agonist activity, docking experiments, molecular dynamics simulations, and MM-PBSA analysis were performed. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.09.045

文献信息

• Synthesis, biological evaluation, and molecular modeling investigation of chiral 2-(4-chloro-phenoxy)-3-phenyl-propanoic acid derivatives with PPARα and PPARγ agonist activity
  作者：Giuseppe Fracchiolla、Antonio Lavecchia、Antonio Laghezza、Luca Piemontese、Raffaella Trisolini、Giuseppe Carbonara、Paolo Tortorella、Ettore Novellino、Fulvio Loiodice

  DOI：10.1016/j.bmc.2008.09.045

  日期：2008.11

  PPARs are ligand-activated transcription factors that govern lipid and glucose homeostasis and play a central role in cardiovascular disease, obesity, and diabetes. Herein, we present screening results for a series of chiral 2-(4-chloro-phenoxy)-3-phenyl-propanoic acid derivatives, some of which are potent PPAR gamma agonists as well as PPAR alpha agonists. To investigate the binding modes of the most interesting derivatives into the PPARa and PPAR gamma binding clefts and evaluate their agonist activity, docking experiments, molecular dynamics simulations, and MM-PBSA analysis were performed. (C) 2008 Published by Elsevier Ltd.