2-amino-4,5-bis(4-chlorophenyl)-N-cyclopropyl-1H-pyrrole-3-carboxamide | 1437869-84-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-amino-4,5-bis(4-chlorophenyl)-N-cyclopropyl-1H-pyrrole-3-carboxamide
• CAS: 1437869-84-5
• 化学式: C₂₀H₁₇Cl₂N₃O
• 分子量: 386.28
• InChiKey: USQXBVKYWZRDHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  70.9
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-amino-N-cyclopropyl-3-iminopropanamide 、 2-bromo-1,2-bis(4-chlorophenyl)ethanone 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以18%的产率得到2-amino-4,5-bis(4-chlorophenyl)-N-cyclopropyl-1H-pyrrole-3-carboxamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 3,4,5-trisubstituted aminothiophenes as inhibitors of p53–MDM2 interaction. Part 2

  摘要：

  Five series of novel 3,4,5-trisubstituted aminothiophene derivatives and analogs were designed and synthesized based on our previous studies. All target compounds were evaluated for their p53-MDM2 binding inhibitory activities and anti-proliferation activities against A549 and PC3 tumor cell lines. Twelve compounds displayed comparable p53-MDM2 binding inhibitory activities to that of Nutlin-3. Among them, compound 7a exhibited marked binding affinity (IC50 = 0.086 mu M). In addition, most target compounds showed potent anti-proliferation activities with IC50 values at low micromolar level. A good selective profile for wild-type p53 expression cell line was also observed. Molecular docking analysis was performed as well to predict possible binding modes of target compounds with MDM2. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.070

文献信息

• Design, synthesis and biological evaluation of novel 3,4,5-trisubstituted aminothiophenes as inhibitors of p53–MDM2 interaction. Part 2
  作者：Weisi Wang、Dan Lv、Ni Qiu、Lei Zhang、Chunqi Hu、Yongzhou Hu

  DOI：10.1016/j.bmc.2013.03.070

  日期：2013.6

  Five series of novel 3,4,5-trisubstituted aminothiophene derivatives and analogs were designed and synthesized based on our previous studies. All target compounds were evaluated for their p53-MDM2 binding inhibitory activities and anti-proliferation activities against A549 and PC3 tumor cell lines. Twelve compounds displayed comparable p53-MDM2 binding inhibitory activities to that of Nutlin-3. Among them, compound 7a exhibited marked binding affinity (IC50 = 0.086 mu M). In addition, most target compounds showed potent anti-proliferation activities with IC50 values at low micromolar level. A good selective profile for wild-type p53 expression cell line was also observed. Molecular docking analysis was performed as well to predict possible binding modes of target compounds with MDM2. (C) 2013 Elsevier Ltd. All rights reserved.