(E)-2-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazinecarbothioamide | 1346145-46-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-2-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazinecarbothioamide
• 英文别名: N-(3,5-dimetoxy-4-hydroxybenzyliden)thiosemicarbazone；[(E)-(4-hydroxy-3,5-dimethoxyphenyl)methylideneamino]thiourea
• CAS: 1346145-46-7
• 化学式: C₁₀H₁₃N₃O₃S
• 分子量: 255.298
• InChiKey: VQIQQYLIOAABJK-LFYBBSHMSA-N

物化性质

• 熔点：
  104 °C(Solvent: Ethanol)
• 沸点：
  445.0±55.0 °C(predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazinecarbothioamide 、 氯乙酸 在 sodium acetate 、 溶剂黄146 作用下， 反应 6.0h， 生成 (E)-2-((E)-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazono)thiazolidin-4-one
  参考文献：
  名称：

  Synthesis of 4-thiazolidinone analogs as potent in vitro anti-urease agents

  摘要：

  4-Thiazolidinone analogs 1-20 were synthesized, characterized by H-1 NMR and EI-MS and investigated for urease inhibitory activity. All twenty (20) analogs exhibited varied degree of urease inhibitory potential with IC50 values 1.73-69.65 mu M, if compared with standard thiourea having IC50 value of 21.25 +/- 0.15 mu M. Among the series, eight derivatives 3, 6, 8, 10, 15, 17, 19, and 20 showed outstanding urease inhibitory potential with IC50 values of 9.34 +/- 0.02, 14.62 +/- 0.03, 8.43 +/- 0.01, 7.3 +/- 0.04, 2.31 +/- 0.002, 5.75 +/- 0.003, 8.81 +/- 0.005, and 1.73 +/- 0.001 mu M, respectively, which is better than the standard thiourea. The remaining analogs showed good to excellent urease inhibition. The binding interactions of these compounds were confirmed through molecular docking studies. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.10.005
• 作为产物：
  描述：

  氨基硫脲 、 丁香醛 以 乙醇 为溶剂， 生成 (E)-2-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 3-thiazolocoumarinyl Schiff-base Derivatives as Cholinesterase Inhibitors

  摘要：

  On the basis of the observed biological activity of the coumarins, a new set of 3‐thiazolocoumarinyl Schiff‐base derivatives with chlorine, hydroxy and methoxy functional group substitutions were designed and synthesized. These compounds were tested against acetylcholinesterase from Electrophorus electricus and butyrylcholinesterase from horse serum and their structure–activity relationship was established. Studies revealed them as the potential inhibitors of cholinesterase (acetylcholinesterase and butyrylcholinesterase). The 3f was found to be most potent against acetylcholinesterase with Ki value of 1.05 ± 0.3 μm and 3l showed excellent inhibitory action against butyrylcholinesterase with Ki value of 0.041 ± 0.002 μm. The synthesized compounds were also docked into the active sites of the homology models of acetylcholinesterase and butyrylcholinesterase to predict the binding modes of these compounds. It was predicted that most of the compounds have similar binding modes with reasonable binding affinities. Our docking studies have also shown that these synthesized compounds have better interaction patterns with butyrylcholinesterase over acetylcholinesterase. The main objective of the study was to develop new potent and selective compounds, which might be further optimized to prevent the progression of the Alzheimer’s disease and could provide symptomatic treatment.

  DOI：

  10.1111/j.1747-0285.2012.01435.x

文献信息

• Synthesis, biological assay in vitro and molecular docking studies of new Schiff base derivatives as potential urease inhibitors
  作者：Muhammad Adil S. Aslam、Shams-ul Mahmood、Mohammad Shahid、Aamer Saeed、Jamshed Iqbal

  DOI：10.1016/j.ejmech.2011.09.009

  日期：2011.11

  A series of new and novel Schiff base derivatives were synthesized and investigated as potential new inhibitors of Jack bean urease. The most potent compounds were 3f with (K-i = 0.09 mu M) and 3k (K-i = 0.122 mu M). A pure competitive mechanism of inhibition was observed. Molecular docking studies were also performed to illustrate the binding mode of the compounds. Docking studies were performed on both enzymes from Jack bean urease and H. pylori urease. It was observed that both share the same binding mode. The binding sites of the two urease structures also aligned very well indicating the similarity in binding sites of the enzymes. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis of 4-thiazolidinone analogs as potent in vitro anti-urease agents
  作者：Fazal Rahim、Khalid Zaman、Hayat Ullah、Muhammad Taha、Abdul Wadood、Muhammad Tariq Javed、Wajid Rehman、Muhammad Ashraf、Reaz Uddin、Imad Uddin、Humna Asghar、Aftab Ahmad Khan、Khalid M. Khan

  DOI：10.1016/j.bioorg.2015.10.005

  日期：2015.12

  4-Thiazolidinone analogs 1-20 were synthesized, characterized by H-1 NMR and EI-MS and investigated for urease inhibitory activity. All twenty (20) analogs exhibited varied degree of urease inhibitory potential with IC50 values 1.73-69.65 mu M, if compared with standard thiourea having IC50 value of 21.25 +/- 0.15 mu M. Among the series, eight derivatives 3, 6, 8, 10, 15, 17, 19, and 20 showed outstanding urease inhibitory potential with IC50 values of 9.34 +/- 0.02, 14.62 +/- 0.03, 8.43 +/- 0.01, 7.3 +/- 0.04, 2.31 +/- 0.002, 5.75 +/- 0.003, 8.81 +/- 0.005, and 1.73 +/- 0.001 mu M, respectively, which is better than the standard thiourea. The remaining analogs showed good to excellent urease inhibition. The binding interactions of these compounds were confirmed through molecular docking studies. (C) 2015 Elsevier Inc. All rights reserved.
• Synthesis and Biological Evaluation of 3-thiazolocoumarinyl Schiff-base Derivatives as Cholinesterase Inhibitors
  作者：Rabia Raza、Aamer Saeed、Mubeen Arif、Shamsul Mahmood、Muhammad Muddassar、Ahsan Raza、Jamshed Iqbal

  DOI：10.1111/j.1747-0285.2012.01435.x

  日期：2012.10

  On the basis of the observed biological activity of the coumarins, a new set of 3‐thiazolocoumarinyl Schiff‐base derivatives with chlorine, hydroxy and methoxy functional group substitutions were designed and synthesized. These compounds were tested against acetylcholinesterase from Electrophorus electricus and butyrylcholinesterase from horse serum and their structure–activity relationship was established. Studies revealed them as the potential inhibitors of cholinesterase (acetylcholinesterase and butyrylcholinesterase). The 3f was found to be most potent against acetylcholinesterase with Ki value of 1.05 ± 0.3 μm and 3l showed excellent inhibitory action against butyrylcholinesterase with Ki value of 0.041 ± 0.002 μm. The synthesized compounds were also docked into the active sites of the homology models of acetylcholinesterase and butyrylcholinesterase to predict the binding modes of these compounds. It was predicted that most of the compounds have similar binding modes with reasonable binding affinities. Our docking studies have also shown that these synthesized compounds have better interaction patterns with butyrylcholinesterase over acetylcholinesterase. The main objective of the study was to develop new potent and selective compounds, which might be further optimized to prevent the progression of the Alzheimer’s disease and could provide symptomatic treatment.