2-[4-(1,3-benzodioxol-5-yloxy)benzylidene]-N-(4-methoxyphenyl)hydrazinecarbothioamide | 1444851-57-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[4-(1,3-benzodioxol-5-yloxy)benzylidene]-N-(4-methoxyphenyl)hydrazinecarbothioamide
• 英文别名: 1-[[4-(1,3-benzodioxol-5-yloxy)phenyl]methylideneamino]-3-(4-methoxyphenyl)thiourea
• CAS: 1444851-57-3
• 化学式: C₂₂H₁₉N₃O₄S
• 分子量: 421.477
• InChiKey: WFTVLKNVFYUMCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  73.34
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  芝麻酚 在 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[4-(1,3-benzodioxol-5-yloxy)benzylidene]-N-(4-methoxyphenyl)hydrazinecarbothioamide
  参考文献：
  名称：

  Augmentation of GABAergic neurotransmission by novel N-(substituted)-2-[4-(substituted)benzylidene]hydrazinecarbothioamides—A potential anticonvulsant approach

  摘要：

  New N-(substituted)-2-[4-(substituted)benzylidene]hydrazinecarbothioamides were designed, synthesized and evaluated for anticonvulsant activity and neurotoxicity. The anticonvulsant activity was established in three seizure models i.e. MES, scMET and 6 Hz model. The most active compound was N-(4-methoxyphenyl)-2-[4-(4-methylphenoxy) benzylidene]hydrazinecarbothioamide PT 30 which showed 100% protection in both MES and 6 Hz test. Compound PT 30 showed protection at three different time points in 6 Hz test at a dose of 100 mg/kg. Compound 2-[4-(4-Chlorophenoxy)benzylidene]-N-cyclohexylhydrazine carbothioamide PT 4 was also found to be active in both MES and 6 Hz test. Titled compounds exhibited good binding properties with epilepsy molecular targets GABA (A) delta and GABA (A) alpha-1 receptors, in LGA based flexible docking studies. Compounds PT 30 and PT 4 were found to elevate gamma-aminobutyric acid (GABA) levels in the midbrain and medulla oblongata regions of rat brain. A computational study was carried out for calculation of pharmacophore pattern and prediction of pharmacokinetic properties. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.019