ethyl 2-methyl-5-phenyl-1-propyl-1H-pyrrole-3-carboxylate | 1220831-29-7

• 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 2-methyl-5-phenyl-1-propyl-1H-pyrrole-3-carboxylate
• CAS: 1220831-29-7
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: CWEMPOYQGDKYBU-UHFFFAOYSA-N

物化性质

• 沸点：
  391.1±30.0 °C(predicted)
• 密度：
  1.03±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  31.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-5-phenyl-1-propyl-1H-pyrrole-3-carboxylate 在 乙醇 、 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 生成 2-methyl-5-phenyl-1-propyl-1H-pyrrole-3-carboxylic acid
  参考文献：
  名称：

  Further optimization of novel pyrrole 3-carboxamides for targeting serotonin 5-HT2A, 5-HT2C, and the serotonin transporter as a potential antidepressant

  摘要：

  In the continuing search for novel compounds targeting serotonin 5-HT2A, 5-HT2C, and serotonin transporter, new arylpiperazine-containing pyrrole 3-carboxamide derivatives were synthesized and evaluated. Based on the lead reported previously, structural modifications regarding N-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propyl)-1,2-dimethyl-5-phenyl-1H-pyrrole-3-carboxamide 5, were accomplished for improvements in not only binding affinity against serotonin receptors and transporter, but also in hERG channel inhibition. Along the line, both the forced swimming tests and spontaneous locomotor activity tests were performed to distinguish between antidepressant activity and false positive results. As potential antidepressant agents, both 2,4-dimethyl-5-phenyl-1H-pyrrole-3-carboxamide and 5-tert-butyl-2-methyl-1H-pyrrole-3-carboxamide derivatives exhibited favorable in vitro and in vivo activities, warranting further investigation around these scaffolds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.037
• 作为产物：
  描述：

  2-甲基-5-苯基-1H-吡咯-3-羧酸乙酯 、 1-碘代丙烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 2-methyl-5-phenyl-1-propyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Arylpiperazine-containing pyrrole 3-carboxamide derivatives targeting serotonin 5-HT2A, 5-HT2C, and the serotonin transporter as a potential antidepressant

  摘要：

  Arylpiperzine-containing pyrrole 3-carboxamide derivatives were synthesized and evaluated as novel antidepressant compounds. The various analogues were efficiently prepared and bio-assayed for binding to 5-HT2A, 5-HT2C receptor, and 5-HT transporter. Based on their in vitro and in vivo activities as well as selectivity over other neurotransmitter receptors and PK profiles, 33 and 34 were identified as lead compounds. Consequently, this pyrrole series of compounds appears to be promising enough to warrant further investigation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.093

文献信息

• Electrochemical synthesis of 1,2,3-trisubstituted pyrroles from β-dicarbonyl compounds, aldehydes and amines via radical addition reaction
  作者：Wei-Jin Chen、Gao-Qing Yuan

  DOI：10.1016/j.tetlet.2021.153615

  日期：2022.2

  An efficient electrochemical synthesis of 1,2,3-trisubstituted pyrroles was developed by one-pot three-component reaction of β-dicarbonyl compounds, aldehydes with amines. The target products could be obtained in good to excellent yields. Our investigations indicate that β-enamino ketone is a key intermediate in this transformation and the reaction mechanism may involve a radical addition reaction

  通过β-二羰基化合物、醛与胺的一锅三组分反应，开发了一种高效的电化学合成1,2,3-三取代吡咯的方法。可以以良好至极好的收率获得目标产物。我们的研究表明，β-烯氨基酮是该转化的关键中间体，反应机理可能涉及自由基加成反应途径。