ethyl 4-(4-bromophenylamino)-2,5-dihydro-5-oxo-2-phenyl-1-propyl-1H-pyrrole-3-carboxylate | 1250289-70-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: ethyl 4-(4-bromophenylamino)-2,5-dihydro-5-oxo-2-phenyl-1-propyl-1H-pyrrole-3-carboxylate
• 英文别名: ethyl 4-(4-bromoanilino)-5-oxo-2-phenyl-1-propyl-2H-pyrrole-3-carboxylate
• CAS: 1250289-70-3
• 化学式: C₂₂H₂₃BrN₂O₃
• 分子量: 443.34
• InChiKey: DNNPUGDVKUWVJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  正丙胺 、 苯甲醛 、 4-溴苯胺 、 丁炔二酸二乙酯 以 乙醇 为溶剂， 以89%的产率得到ethyl 4-(4-bromophenylamino)-2,5-dihydro-5-oxo-2-phenyl-1-propyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  A novel class of small-molecule caspase-3 inhibitors prepared by multicomponent reactions

  摘要：

  A series of tetra- and pentasubstituted polyfunctional dihydropyrroles 5 and 6 were synthesized via practical multicomponent reactions (MCRs) for research on their structure activity relationship as caspase-3 inhibitors. Among 39 compounds evaluated, 14 of them exhibited inhibition against caspase-3 with IC50 ranging from 5 to 20 mu M. The inhibitory activities of 5 and 6 depend on the nature of substituents on different positions. 5 and 6 possess a different scaffold from those previously reported and are the first caspase-3 inhibitors prepared via MCRs. The most active compounds 5k (IC50 = 5.27 mu M) could therefore be used as a lead for the development of highly potent caspase-3 inhibitors as drug candidates for therapeutic agents by taking advantage of MCRs. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.001

文献信息

• A novel class of small-molecule caspase-3 inhibitors prepared by multicomponent reactions
  作者：Qiuhua Zhu、Lixin Gao、Zhipeng Chen、Sichao Zheng、Huafei Shu、Jia Li、Huanfeng Jiang、Shuwen Liu

  DOI：10.1016/j.ejmech.2012.05.001

  日期：2012.8

  A series of tetra- and pentasubstituted polyfunctional dihydropyrroles 5 and 6 were synthesized via practical multicomponent reactions (MCRs) for research on their structure activity relationship as caspase-3 inhibitors. Among 39 compounds evaluated, 14 of them exhibited inhibition against caspase-3 with IC50 ranging from 5 to 20 mu M. The inhibitory activities of 5 and 6 depend on the nature of substituents on different positions. 5 and 6 possess a different scaffold from those previously reported and are the first caspase-3 inhibitors prepared via MCRs. The most active compounds 5k (IC50 = 5.27 mu M) could therefore be used as a lead for the development of highly potent caspase-3 inhibitors as drug candidates for therapeutic agents by taking advantage of MCRs. (C) 2012 Elsevier Masson SAS. All rights reserved.