ethyl 1-(4-cyanobenzyl)-1H-pyrrole-2-carboxylate | 1138159-54-2

• 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 1-(4-cyanobenzyl)-1H-pyrrole-2-carboxylate
• 英文别名: Ethyl 1-[(4-cyanophenyl)methyl]pyrrole-2-carboxylate；ethyl 1-[(4-cyanophenyl)methyl]pyrrole-2-carboxylate
• CAS: 1138159-54-2
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: SBAJWCJOYDJOJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-(4-cyanobenzyl)-1H-pyrrole-2-carboxylate 在 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、600.01 kPa 条件下， 以98%的产率得到ethyl 1-(4-(aminomethyl)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
• 作为产物：
  描述：

  吡咯-2-羧酸乙酯 、 对氰基溴化苄 在 四丁基碘化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到ethyl 1-(4-cyanobenzyl)-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