4,4'-((3-(3,5-difluorophenylsulfonamido)pyridine-2,6-diyl)bis(oxy))bis(N'-acetoxybenzimidamide) | 1256591-05-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4'-((3-(3,5-difluorophenylsulfonamido)pyridine-2,6-diyl)bis(oxy))bis(N'-acetoxybenzimidamide)
• CAS: 1256591-05-5
• 化学式: C₂₉H₂₄F₂N₆O₈S
• 分子量: 654.608
• InChiKey: WHGFRINMQWOSDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  46.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  201.88
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  4,4'-((3-(3,5-difluorophenylsulfonamido)pyridine-2,6-diyl)bis(oxy))bis(N'-acetoxybenzimidamide) 在 溶剂黄146 、 锌 作用下， 以0.05 g的产率得到4,4'-((3-(3,5-difluorophenylsulfonamido)pyridine-2,6-diyl)bis(oxy))dibenzimidamide
  参考文献：
  名称：

  Discovery of Pyridyl Bis(oxy)dibenzimidamide Derivatives as Selective Matriptase Inhibitors

  摘要：

  Matriptase belongs to trypsin-like serine proteases involved in matrix remodeling/degradation, growth regulation, survival, motility, and cell morphogenesis. Herein, we report a structure-based approach, which led to the discovery of sulfonamide and amide derivatives of pyridyl bis(oxy)benzamidine as potent and selective matriptase inhibitors. Co-crystal structures of selected compounds in complex with matriptase supported compound designing. Additionally, WaterMap analyses indicated the possibility of occupying a distinct pocket within the catalytic domain, exploration of which resulted in >100-fold improvement in potency. Co-crystal structure of 10 with matriptase revealed critical interactions leading to potent target inhibition and selectivity against other senile proteases.

  DOI：

  10.1021/ml400213v
• 作为产物：
  描述：

  4,4'-((3-nitropyridine-2,6-diyl)bis(oxy))dibenzonitrile 在 盐酸羟胺 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 锌 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 21.0h， 生成 4,4'-((3-(3,5-difluorophenylsulfonamido)pyridine-2,6-diyl)bis(oxy))bis(N'-acetoxybenzimidamide)
  参考文献：
  名称：

  Discovery of Pyridyl Bis(oxy)dibenzimidamide Derivatives as Selective Matriptase Inhibitors

  摘要：

  Matriptase belongs to trypsin-like serine proteases involved in matrix remodeling/degradation, growth regulation, survival, motility, and cell morphogenesis. Herein, we report a structure-based approach, which led to the discovery of sulfonamide and amide derivatives of pyridyl bis(oxy)benzamidine as potent and selective matriptase inhibitors. Co-crystal structures of selected compounds in complex with matriptase supported compound designing. Additionally, WaterMap analyses indicated the possibility of occupying a distinct pocket within the catalytic domain, exploration of which resulted in >100-fold improvement in potency. Co-crystal structure of 10 with matriptase revealed critical interactions leading to potent target inhibition and selectivity against other senile proteases.

  DOI：

  10.1021/ml400213v