ethyl 1-(3-((3-((3s,5s,7s)-adamantan-1-yl)ureido)methyl)benzyl)-1H-pyrrole-2-carboxylate | 1414361-87-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 1-(3-((3-((3s,5s,7s)-adamantan-1-yl)ureido)methyl)benzyl)-1H-pyrrole-2-carboxylate
• 英文别名: Ethyl 1-[[3-[(1-adamantylcarbamoylamino)methyl]phenyl]methyl]pyrrole-2-carboxylate；ethyl 1-[[3-[(1-adamantylcarbamoylamino)methyl]phenyl]methyl]pyrrole-2-carboxylate
• CAS: 1414361-87-7
• 化学式: C₂₆H₃₃N₃O₃
• 分子量: 435.566
• InChiKey: RLJKFIQBNSVEKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  72.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-(3-((3-((3s,5s,7s)-adamantan-1-yl)ureido)methyl)benzyl)-1H-pyrrole-2-carboxylate 在 水 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.25h， 以50%的产率得到1-(3-((3-((3s,5s,7s)-adamantan-1-yl)ureido)methyl)benzyl)-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Design and Synthesis of Dual Modulators of Soluble Epoxide Hydrolase and Peroxisome Proliferator-Activated Receptors

  摘要：

  Metabolic syndrome is a complex condition which often requires the use of multiple medications as a treatment. The resulting problems of polypharmacy are increase in side effects, drug-drug interactions, and its high economic cost. Development of multitarget compounds is a promising strategy to avoid the complications arising from administration of multiple drugs. Modulators of peroxisome proliferator-activated receptors (PPARs) are established agents in the treatment of dyslipidaemia, hyperglycaemia, and insulin resistance. Inhibitors of soluble epoxide hydrolase (sEH) are under evaluation for their use in cardiovascular diseases. In the present study, a series of dual sEH/PPAR modulators containing a pyrrole acidic headgroup and a urea pharmacophore were designed, synthesized, and evaluated in vitro using recombinant enzyme and cell-based assays. Compounds with different activity profiles were obtained which could be used in the treatment of metabolic syndrome.

  DOI：

  10.1021/jm301194c
• 作为产物：
  描述：

  3-氰基苄基溴 在 氢气 、 四丁基碘化铵 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、600.01 kPa 条件下， 反应 12.0h， 生成 ethyl 1-(3-((3-((3s,5s,7s)-adamantan-1-yl)ureido)methyl)benzyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Design and Synthesis of Dual Modulators of Soluble Epoxide Hydrolase and Peroxisome Proliferator-Activated Receptors

  摘要：

  Metabolic syndrome is a complex condition which often requires the use of multiple medications as a treatment. The resulting problems of polypharmacy are increase in side effects, drug-drug interactions, and its high economic cost. Development of multitarget compounds is a promising strategy to avoid the complications arising from administration of multiple drugs. Modulators of peroxisome proliferator-activated receptors (PPARs) are established agents in the treatment of dyslipidaemia, hyperglycaemia, and insulin resistance. Inhibitors of soluble epoxide hydrolase (sEH) are under evaluation for their use in cardiovascular diseases. In the present study, a series of dual sEH/PPAR modulators containing a pyrrole acidic headgroup and a urea pharmacophore were designed, synthesized, and evaluated in vitro using recombinant enzyme and cell-based assays. Compounds with different activity profiles were obtained which could be used in the treatment of metabolic syndrome.

  DOI：

  10.1021/jm301194c

文献信息

• Design and Synthesis of Dual Modulators of Soluble Epoxide Hydrolase and Peroxisome Proliferator-Activated Receptors
  作者：Estel.la Buscató、René Blöcher、Christina Lamers、Franca-Maria Klingler、Steffen Hahn、Dieter Steinhilber、Manfred Schubert-Zsilavecz、Ewgenij Proschak

  DOI：10.1021/jm301194c

  日期：2012.12.13

  Metabolic syndrome is a complex condition which often requires the use of multiple medications as a treatment. The resulting problems of polypharmacy are increase in side effects, drug-drug interactions, and its high economic cost. Development of multitarget compounds is a promising strategy to avoid the complications arising from administration of multiple drugs. Modulators of peroxisome proliferator-activated receptors (PPARs) are established agents in the treatment of dyslipidaemia, hyperglycaemia, and insulin resistance. Inhibitors of soluble epoxide hydrolase (sEH) are under evaluation for their use in cardiovascular diseases. In the present study, a series of dual sEH/PPAR modulators containing a pyrrole acidic headgroup and a urea pharmacophore were designed, synthesized, and evaluated in vitro using recombinant enzyme and cell-based assays. Compounds with different activity profiles were obtained which could be used in the treatment of metabolic syndrome.