1-Naphthylhydrazon-brenztraubensaeure | 42178-82-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Naphthylhydrazon-brenztraubensaeure
• 英文别名: Pyruvic-acid-α-naphthylhydrazone；2-[1]naphthylhydrazono-propionic acid；Brenztraubensaeure-α-naphthylhydrazon；2-[1]Naphthylhydrazono-propionsaeure；Pyruvic acid naphthylhydrazone；2-(naphthalen-1-ylhydrazinylidene)propanoic acid
• CAS: 42178-82-5
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: NSDQQWMQWYZQHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙醇 、 1-Naphthylhydrazon-brenztraubensaeure 在 硫酸 作用下， 生成 2-[1]naphthylhydrazono-propionic acid ethyl ester
  参考文献：
  名称：

  Schlieper, Justus Liebigs Annalen der Chemie, 1887, vol. 239, p. 237

  摘要：

  DOI：
• 作为产物：
  描述：

  萘酚 在 盐酸 、 一水合肼 作用下， 以 水 为溶剂， 反应 12.0h， 生成 1-Naphthylhydrazon-brenztraubensaeure
  参考文献：
  名称：

  A novel potent metal-binding NDM-1 inhibitor was identified by fragment virtual, SPR and NMR screening

  摘要：

  NDM-1 can hydrolyze nearly all available β-lactam antibiotics, including carbapenems. NDM-1 producing bacterial strains are worldwide threats. It is still very challenging to find a potent NDM-1 inhibitor for clinical use. In our study, we used a metal-binding pharmacophore (MBP) enriched virtual fragment library to screen NDM-1 hits. SPR screening helped to verify the MBP virtual hits and identified a new NDM-1 binder and weak inhibitor A1. A solution NMR study of ¹⁵N-labeled NDM-1 showed that A1 disturbed all three residues coordinating the second zinc ion (Zn2) in the active pocket of NDM-1. The perturbation only happened in the presence of zinc ion, indicating that A1 bound to Zn2. Based on the scaffold of A1, we designed and synthesized a series of NDM-1 inhibitors. Several compounds showed synergistic antibacterial activity with meropenem against NDM-1 producing K. pneumoniae.

  DOI：

  10.1016/j.bmc.2020.115437

文献信息

• Fischer,E., Justus Liebigs Annalen der Chemie, 1886, vol. 232, p. 237
  作者：Fischer,E.

  DOI：——

  日期：——
• A novel potent metal-binding NDM-1 inhibitor was identified by fragment virtual, SPR and NMR screening
  作者：Huifang Guo、Kai Cheng、Yan Gao、Weiqi Bai、Cai Wu、Wei He、Conggang Li、Zhuorong Li

  DOI：10.1016/j.bmc.2020.115437

  日期：2020.5

  NDM-1 can hydrolyze nearly all available β-lactam antibiotics, including carbapenems. NDM-1 producing bacterial strains are worldwide threats. It is still very challenging to find a potent NDM-1 inhibitor for clinical use. In our study, we used a metal-binding pharmacophore (MBP) enriched virtual fragment library to screen NDM-1 hits. SPR screening helped to verify the MBP virtual hits and identified a new NDM-1 binder and weak inhibitor A1. A solution NMR study of ¹⁵N-labeled NDM-1 showed that A1 disturbed all three residues coordinating the second zinc ion (Zn2) in the active pocket of NDM-1. The perturbation only happened in the presence of zinc ion, indicating that A1 bound to Zn2. Based on the scaffold of A1, we designed and synthesized a series of NDM-1 inhibitors. Several compounds showed synergistic antibacterial activity with meropenem against NDM-1 producing K. pneumoniae.
• Schlieper, Justus Liebigs Annalen der Chemie, 1887, vol. 239, p. 237
  作者：Schlieper

  DOI：——

  日期：——