ethyl 3-(4-bromophenyl)-2-(2H-1,2,3-triazol-2-yl)propanoate | 1196548-24-9

• 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: ethyl 3-(4-bromophenyl)-2-(2H-1,2,3-triazol-2-yl)propanoate
• 英文别名: Ethyl 3-(4-bromophenyl)-2-(triazol-2-yl)propanoate
• CAS: 1196548-24-9
• 化学式: C₁₃H₁₄BrN₃O₂
• 分子量: 324.177
• InChiKey: DELMPPQCABOPBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[3-(9-Borabicyclo[3.3.1]nonan-9-yl)propyl]-5-methyl-2-phenyl-1,3-oxazole 、 ethyl 3-(4-bromophenyl)-2-(2H-1,2,3-triazol-2-yl)propanoate 在 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 三苯胂 、 caesium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以2.11 g的产率得到3-{4-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-phenyl}-2-1,2,3-triazol-2-yl-propionic acid ethyl ester
  参考文献：
  名称：

  Synthesis and evaluation of novel α-heteroaryl-phenylpropanoic acid derivatives as PPARα/γ dual agonists

  摘要：

  The synthesis of a new series of phenylpropanoic acid derivatives incorporating an heteroaryl group at the alpha-position and their evaluation for binding and activation of PPAR alpha and PPAR gamma are presented in this report. Among the new compounds, (S)-3-{4-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-phenyl}-2-1,2,3- triazol-2-yl-propionic acid (17j), was identified as a potent human PPAR alpha/gamma dual agonist (EC50 = 0.013 and 0.061 mu M, respectively) with demonstrated oral bioavailability in rat and dog. 17j was shown to decrease insulin levels, plasma glucose, and triglycerides in the ZDF female rat model. In the human apolipoprotein A-1/CETP transgenic mouse model 17j produced increases in hApoA1 and HDL-C and decreases in plasma triglycerides. The increased potency for binding and activation of both PPAR subtypes observed with 17j when compared to previous analogs in this series was explained based on results derived from crystallographic and modeling studies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.001
• 作为产物：
  描述：

  对溴溴苄 、 2H-1,2,3-噻唑-2-乙酸乙酯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以26%的产率得到ethyl 3-(4-bromophenyl)-2-(2H-1,2,3-triazol-2-yl)propanoate
  参考文献：
  名称：

  Synthesis and evaluation of novel α-heteroaryl-phenylpropanoic acid derivatives as PPARα/γ dual agonists

  摘要：

  The synthesis of a new series of phenylpropanoic acid derivatives incorporating an heteroaryl group at the alpha-position and their evaluation for binding and activation of PPAR alpha and PPAR gamma are presented in this report. Among the new compounds, (S)-3-{4-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-phenyl}-2-1,2,3- triazol-2-yl-propionic acid (17j), was identified as a potent human PPAR alpha/gamma dual agonist (EC50 = 0.013 and 0.061 mu M, respectively) with demonstrated oral bioavailability in rat and dog. 17j was shown to decrease insulin levels, plasma glucose, and triglycerides in the ZDF female rat model. In the human apolipoprotein A-1/CETP transgenic mouse model 17j produced increases in hApoA1 and HDL-C and decreases in plasma triglycerides. The increased potency for binding and activation of both PPAR subtypes observed with 17j when compared to previous analogs in this series was explained based on results derived from crystallographic and modeling studies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.001

文献信息

• Preparation of N2-alkylated 1,2,3-triazoles
  申请人：——

  公开号：US20040266848A1

  公开（公告）日：2004-12-30

  Methods and materials for preparing N2-alkylated triazoles, such as 3-{4-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-phenyl}-2-[1,2,3]triazol-2-yl-propionic acid, are disclosed. Such compounds are PPAR agonists that are useful for treating non-insulin dependent diabetes.

  揭示了用于制备N2-烷基化三唑类化合物的方法和材料，例如3-【4-【3-(5-甲基-2-苯基-噁唑-4-基)-丙基】-苯基】-2-【1,2,3】三唑-2-基丙酸。这些化合物是PPAR激动剂，可用于治疗非胰岛素依赖型糖尿病。
• PREPARATION OF N2-ALKYLATED 1,2,3-TRIAZOLES
  申请人：Warner-Lambert Company LLC

  公开号：EP1641788A1

  公开（公告）日：2006-04-05
• [EN] PREPARATION OF N2-ALKYLATED 1,2,3-TRIAZOLES<br/>[FR] PREPARATION DE 1,2,3-TRIAZOLES N2-ALKYLES
  申请人：WARNER LAMBERT CO

  公开号：WO2005000841A1

  公开（公告）日：2005-01-06

  Methods and materials for preparing N2-alkylated triazoles, such as 3-4-[3­(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-phenyl}-2- [1,2,3]triazol-2-yl-propionic acid, are disclosed. Such compounds are PPAR agonists that are useful for treating non­ insulin dependent diabetes.