1-(2-methylbenzylidene)-2-[4-(4-chlorophenyl)thiazol-2-yl]hydrazine | 1011946-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-methylbenzylidene)-2-[4-(4-chlorophenyl)thiazol-2-yl]hydrazine
• 英文别名: 4-(4-chlorophenyl)-N-[(2-methylphenyl)methylideneamino]-1,3-thiazol-2-amine
• CAS: 1011946-35-2
• 化学式: C₁₇H₁₄ClN₃S
• 分子量: 327.837
• InChiKey: XQNUPJAIVZMYNN-UHFFFAOYSA-N

物化性质

• 熔点：
  210-212 °C
• 沸点：
  500.9±52.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.28
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-甲基苯甲醛 以 异丙醇 为溶剂， 生成 1-(2-methylbenzylidene)-2-[4-(4-chlorophenyl)thiazol-2-yl]hydrazine
  参考文献：
  名称：

  Synthesis and biological assessment of novel 2-thiazolylhydrazones and computational analysis of their recognition by monoamine oxidase B

  摘要：

  Monoamine oxidase B (MAO-B) is a promising target for the treatment of neurodegenerative disorders. We report the synthesis and the biological evaluation of halogenated derivatives of 1-aryliden-2-(4-phenylthiazol-2-yl)hydrazines. The fluorinated series shows interesting activity and great selectivity toward the human recombinant MAO-B isoform expressed in baculovirus infected BTI insect cells. The multiple crystal structures alignment of the enzyme highlighted pronounced induced fit (IF) adaptations with respect to bound ligands. Therefore, IF docking (IFD) experiments and molecular dynamic (MD) simulations were carried out to reveal the putative binding mode and to explain the experimentally observed differences in the activity of 1-(aryliden-2-(4-(4-chlorophenyl)thiazol-2-yl)hydrazines. The importance of water molecules within the binding site was also investigated. These are known to play an important role in the binding site cavity and to mediate protein ligand interactions. Detailed analyses of the trajectories provide insights on the chemical features required for the activity of this scaffold. In particular it was highlighted the importance of fluorine atom interacting with the water close to the cofactor and the influence of steric bulkiness of substituents in the arylidene moiety. Free energy perturbation (FEP) analysis confirmed experimental data. The information we deduced will help to develop novel high-affinity MAO-B inhibitors. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.12.027