4-[5-[1-(3-Chloro-4-piperazin-1-ylphenyl)imidazol-2-yl]furan-2-yl]benzonitrile | 1620476-91-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-[5-[1-(3-Chloro-4-piperazin-1-ylphenyl)imidazol-2-yl]furan-2-yl]benzonitrile
• 英文别名: 4-[5-[1-(3-chloro-4-piperazin-1-ylphenyl)imidazol-2-yl]furan-2-yl]benzonitrile
• CAS: 1620476-91-6
• 化学式: C₂₄H₂₀ClN₅O
• 分子量: 429.909
• InChiKey: NZOZJWYMJYUXGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(5-formylfuran-2-yl)benzonitrile 在 aluminum oxide 、 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 N,N-二异丙基乙胺 、 锌 作用下， 生成 4-[5-[1-(3-Chloro-4-piperazin-1-ylphenyl)imidazol-2-yl]furan-2-yl]benzonitrile
  参考文献：
  名称：

  Discovery of a novel series of potent MK2 non-ATP competitive inhibitors using 1,2-substituted azoles as cis-amide isosteres

  摘要：

  A unified strategy was conceived and implemented to deliver conformationally constrained anilides based on their preferred cis-amide conformers. The imidazole/triazole mimicing amide bonds were designed, building upon an earlier discovery of a novel series of tricyclic lactams MK2 kinase inhibitors. This approach enabled rapid, modular synthesis of structurally novel analogs. The efficient SAR development led to the discovery of low molecular weight and potent MK2 non-ATP competitive inhibitors with good ligand efficiency, which led to improved permeability and oral exposure in rats. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.024

文献信息

• Discovery of a novel series of potent MK2 non-ATP competitive inhibitors using 1,2-substituted azoles as cis-amide isosteres
  作者：Dong Xiao、Xiaohong Zhu、Michael Sofolarides、Sylvia Degrado、Ning Shao、Ashwin Rao、Xiao Chen、Robert Aslanian、James Fossetta、Fang Tian、Prashant Trivedi、Daniel Lundell、Anandan Palani

  DOI：10.1016/j.bmcl.2014.05.024

  日期：2014.8

  A unified strategy was conceived and implemented to deliver conformationally constrained anilides based on their preferred cis-amide conformers. The imidazole/triazole mimicing amide bonds were designed, building upon an earlier discovery of a novel series of tricyclic lactams MK2 kinase inhibitors. This approach enabled rapid, modular synthesis of structurally novel analogs. The efficient SAR development led to the discovery of low molecular weight and potent MK2 non-ATP competitive inhibitors with good ligand efficiency, which led to improved permeability and oral exposure in rats. (C) 2014 Elsevier Ltd. All rights reserved.