(S)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethylamino]phenyl}-2-pyrrol-1-yl-propionic acid methyl ester | 1038923-49-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethylamino]phenyl}-2-pyrrol-1-yl-propionic acid methyl ester
• CAS: 1038923-49-7
• 化学式: C₂₆H₂₇N₃O₃
• 分子量: 429.519
• InChiKey: HUJCWGNXDRFPQZ-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  69.29
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethylamino]phenyl}-2-pyrrol-1-yl-propionic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以78%的产率得到Phenylpropanoic acid derivative, 66
  参考文献：
  名称：

  Effects of modifications of the linker in a series of phenylpropanoic acid derivatives: Synthesis, evaluation as PPARα/γ dual agonists, and X-ray crystallographic studies

  摘要：

  A new series of alpha-aryl or alpha-heteroarylphenyl propanoic acid derivatives was synthesized that incorporate acetylene-, ethylene-, propyl-, or nitrogen-derived linkers as a replacement of the commonly used ether moiety that joins the central phenyl ring with the lipophilic tail. The effect of these modi. cations in the binding and activation of PPAR alpha and PPAR gamma was first evaluated in vitro. Compounds possessing suitable profiles were then evaluated in the ob/ob mouse model of type 2 diabetes. The propylene derivative 40 and the propyl derivative 53 demonstrated robust plasma glucose lowering activity in this model. Compound 53 was also evaluated in male Zucker diabetic fatty rats and was found to achieve normalization of glucose, triglycerides, and insulin levels. An X-ray crystal structure of the complex of 53 with the PPAR gamma-ligand-binding domain was obtained and discussed in this report. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.043
• 作为产物：
  描述：

  (5-methyl-2-phenyl-oxazol-4-yl)acetaldehyde 、 (S)-3-(4-aminophenyl)-2-pyrrol-1-yl-propionic acid methyl ester 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以35%的产率得到(S)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethylamino]phenyl}-2-pyrrol-1-yl-propionic acid methyl ester
  参考文献：
  名称：

  Effects of modifications of the linker in a series of phenylpropanoic acid derivatives: Synthesis, evaluation as PPARα/γ dual agonists, and X-ray crystallographic studies

  摘要：

  A new series of alpha-aryl or alpha-heteroarylphenyl propanoic acid derivatives was synthesized that incorporate acetylene-, ethylene-, propyl-, or nitrogen-derived linkers as a replacement of the commonly used ether moiety that joins the central phenyl ring with the lipophilic tail. The effect of these modi. cations in the binding and activation of PPAR alpha and PPAR gamma was first evaluated in vitro. Compounds possessing suitable profiles were then evaluated in the ob/ob mouse model of type 2 diabetes. The propylene derivative 40 and the propyl derivative 53 demonstrated robust plasma glucose lowering activity in this model. Compound 53 was also evaluated in male Zucker diabetic fatty rats and was found to achieve normalization of glucose, triglycerides, and insulin levels. An X-ray crystal structure of the complex of 53 with the PPAR gamma-ligand-binding domain was obtained and discussed in this report. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.043