ethyl 1-ethyl-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate | 879329-60-9

• 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-ethyl-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate
• 英文别名: ethyl 1-ethyl-2-methyl-5-phenylpyrrole-3-carboxylate
• CAS: 879329-60-9
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: UZDWJVXXZWLSHY-UHFFFAOYSA-N

物化性质

• 熔点：
  64-66 °C(Solv: ethanol (64-17-5))
• 沸点：
  377.3±30.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 1-ethyl-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-乙基-2-甲基-5-苯基-3-吡咯羧酸
  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
• 作为产物：
  描述：

  2-甲基-5-苯基-1H-吡咯-3-羧酸乙酯 、 碘乙烷 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 生成 ethyl 1-ethyl-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate
  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

文献信息

• Sonochemically assisted synthesis of N-substituted pyrroles catalyzed by ZnO nanoparticles under solvent-free conditions
  作者：Ashraf S Shahvelayati、Maryam Sabbaghan、Solmaz Banihashem

  DOI：10.1007/s00706-016-1904-6

  日期：2017.6

  AbstractAn efficient and rapid synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives from a one-pot multicomponent reaction of amines, 1,3-dicarbonyl compounds, and α-haloketones in the presence of ZnO nanoparticles catalyst under ultrasonic irradiation and solvent-free conditions is described. Graphical abstract

  摘要在超声波辐射和溶剂作用下，在ZnO纳米颗粒催化剂存在下，由胺，1,3-二羰基化合物和α-卤代烃的一锅多组分反应快速高效地合成1,2,3,5-四取代的吡咯衍生物描述了无条件。 图形概要