4-(2,4-difluorophenyl)-2-(2-(2-methylcyclohexylidene)hydrazineyl)thiazole | 1049014-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(2,4-difluorophenyl)-2-(2-(2-methylcyclohexylidene)hydrazineyl)thiazole
• CAS: 1049014-22-3
• 化学式: C₁₆H₁₇F₂N₃S
• 分子量: 321.394
• InChiKey: GBSDYRSNVCORPF-UHFFFAOYSA-N

物化性质

• 熔点：
  157-160 °C
• 沸点：
  438.6±53.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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-溴-2',4'-二氟苯乙酮 、 2-methylcyclohexanone thiosemicarbazone 以 异丙醇 为溶剂， 反应 2.0h， 以68%的产率得到4-(2,4-difluorophenyl)-2-(2-(2-methylcyclohexylidene)hydrazineyl)thiazole
  参考文献：
  名称：

  Synthesis, Stereochemical Identification, and Selective Inhibitory Activity against Human Monoamine Oxidase-B of 2-Methylcyclohexylidene-(4-arylthiazol-2-yl)hydrazones

  摘要：

  A series of 2-methylcyclohexylidene-(4-arylthiazol-2-yl)hydrazones have been investigated for their ability to inhibit selectively the activity of the human A and B isoforms of monoamine oxidase (MAO). The target compounds, which present a stereogenic center on the cyclohexane ring, were obtained as pure (R) and (S) enantiomers by enantioselective HPLC. The absolute configuration of homochiral forms isolated on a semipreparative scale was obtained by a combined strategy based on chemical correlation and single-crystal X-ray diffraction. All compounds showed higher activity against the human MAO-B isoform with IC(50) values ranging between 26.81 +/- 2.74 mu M and 14.20 +/- 0.26 nM, and the assays carried out on the pure enantiomers showed higher activity for the (R) form. A computational study was performed by molecular mechanics, DFT-based quantomechanics, and docking techniques on the most active and human MAO-B selective inhibitor 8.

  DOI：

  10.1021/jm800132g