(E)-1-(2,4-dihydroxybenzylidene)-4-(pyridin-4-yl)semicarbazide | 1450600-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-1-(2,4-dihydroxybenzylidene)-4-(pyridin-4-yl)semicarbazide
• 英文别名: 1-[(E)-(2,4-dihydroxyphenyl)methylideneamino]-3-pyridin-4-ylurea
• CAS: 1450600-78-8
• 化学式: C₁₃H₁₂N₄O₃
• 分子量: 272.263
• InChiKey: KYHXKWDXJRGIMV-OVCLIPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(pyridin-4-yl)urea 在 一水合肼 、 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 (E)-1-(2,4-dihydroxybenzylidene)-4-(pyridin-4-yl)semicarbazide
  参考文献：
  名称：

  Synthesis, evaluation and molecular dynamics study of some new 4-aminopyridine semicarbazones as an antiamnesic and cognition enhancing agents

  摘要：

  Some new semicarbazones of 4-aminopyridine were synthesized and evaluated for antiamnesic, cognition enhancing and anticholinesterase activities. The results illustrated a significant cognition enhancing effect on elevated plus maze model with a significant reversal of scopolamine-induced amnesia. A significant inhibition in acetycholinesterase (AChE) activity by all the synthesized compounds in specific brain regions that is, prefrontal cortex, hippocampus and hypothalamus was observed. Compound 4APi exhibited significant antiamnesic and cognition enhancing activity which was comparable with standard drug donepezil. Its enzyme kinetic study revealed a non-competitive inhibition of AChE and a competitive inhibition of butyrylcholinesterase (BChE). Docking studies predicted the binding modes of these compounds in AChE active site, which were further processed for molecular dynamics simulation for calculating binding free energies using Molecular Mechanics-Generalized Born Surface Area (MM/GBSA). All the computational study confirmed their consensual interaction with AChE justifying the experimental outcome. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.003

文献信息

• Synthesis, evaluation and molecular dynamics study of some new 4-aminopyridine semicarbazones as an antiamnesic and cognition enhancing agents
  作者：Saurabh K. Sinha、Sushant K. Shrivastava

  DOI：10.1016/j.bmc.2013.06.003

  日期：2013.9

  Some new semicarbazones of 4-aminopyridine were synthesized and evaluated for antiamnesic, cognition enhancing and anticholinesterase activities. The results illustrated a significant cognition enhancing effect on elevated plus maze model with a significant reversal of scopolamine-induced amnesia. A significant inhibition in acetycholinesterase (AChE) activity by all the synthesized compounds in specific brain regions that is, prefrontal cortex, hippocampus and hypothalamus was observed. Compound 4APi exhibited significant antiamnesic and cognition enhancing activity which was comparable with standard drug donepezil. Its enzyme kinetic study revealed a non-competitive inhibition of AChE and a competitive inhibition of butyrylcholinesterase (BChE). Docking studies predicted the binding modes of these compounds in AChE active site, which were further processed for molecular dynamics simulation for calculating binding free energies using Molecular Mechanics-Generalized Born Surface Area (MM/GBSA). All the computational study confirmed their consensual interaction with AChE justifying the experimental outcome. (C) 2013 Elsevier Ltd. All rights reserved.