1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(benzodioxol-5-ylmethylene)-hydrazine | 1242658-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(benzodioxol-5-ylmethylene)-hydrazine
• CAS: 1242658-53-2
• 化学式: C₁₈H₁₅N₃O₃S
• 分子量: 353.401
• InChiKey: QLTYHEGFWYZRHL-UHFFFAOYSA-N

物化性质

• 熔点：
  229-230 °C
• 沸点：
  537.5±60.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  64.97
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  (1,3-苯并二氧戊环-5-基亚甲基氨基)硫脲 、 2-溴-3‘-甲氧基苯乙酮 以 乙醇 为溶剂， 反应 4.0h， 生成 1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(benzodioxol-5-ylmethylene)-hydrazine
  参考文献：
  名称：

  Investigations on the 2-thiazolylhydrazyne scaffold: Synthesis and molecular modeling of selective human monoamine oxidase inhibitors

  摘要：

  A new series of [4-(3-methoxyphenyl)-thiazol-2-yl]hydrazyne derivatives were synthesized in good yield (71-99%) and characterized by elemental analysis and H-1 NMR studies. The compounds were assayed for their in vitro human monoamine oxidase (hMAO) inhibitory activity and selectivity and most of them showed IC50 values in the nanomolar range, thus demonstrating our interest in this privileged scaffold. The most active and selective derivative (20), bearing a pyridine moiety on the C=N, displayed IC50 = 3.81 +/- 0.12 nM and selectivity ratio = 119 toward hMAO-B. Molecular modeling studies were carried out on recent and high resolution hMAO-A and hMAO-B crystallographic structures to better justify the enzyme-inhibitor interaction toward hMAO isoforms and to explain the structure-activity relationship of this kind of inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.007