(E)-3-(2-(2-(4-nitrobenzylidene)hydrazinyl)thiazol-4-yl)-2H-chromen-2-one | 1408316-03-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (E)-3-(2-(2-(4-nitrobenzylidene)hydrazinyl)thiazol-4-yl)-2H-chromen-2-one
• 英文别名: 3-{2-[(2E)-2-(4-nitrobenzylidene)hydrazinyl]-1,3-thiazol-4-yl}-2H-chromen-2-one；3-[2-[(2E)-2-[(4-nitrophenyl)methylidene]hydrazinyl]-1,3-thiazol-4-yl]chromen-2-one
• CAS: 1408316-03-9
• 化学式: C₁₉H₁₂N₄O₄S
• 分子量: 392.395
• InChiKey: NZRHBPFXGMWXIU-KEBDBYFISA-N

物化性质

• 沸点：
  650.8±65.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  水杨醛 在 哌啶 、 溴 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 (E)-3-(2-(2-(4-nitrobenzylidene)hydrazinyl)thiazol-4-yl)-2H-chromen-2-one
  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, photophysical and electrochemical properties of donor–acceptor type hydrazinyl thiazolyl coumarins
  作者：Kumar Godugu、Thrivikram Reddy Gundala、Ramakrishna Bodapati、Venkata Divya Sri Yadala、Subramanyam Sarma Loka、Chinna Gangi Reddy Nallagondu

  DOI：10.1039/d0nj00082e

  日期：——

  scaled up to a gram level. Moreover, the catalyst can be reused 7 times without significant change of activity. The photophysical properties of the synthesized D–A type HTCs are also studied and it was noticed that the fluorescence properties can be varied with the position of electron donating group on the aromatic ring of aldehyde/ketone of HTCs. Most of the compounds exhibited bright fluorescence

  已经开发了一种水介导的MCR策略，用于通过芳香醛的三组分反应以优异的分离产率（90-98％）合成供体（D）-受体（A）型肼基噻唑基香豆素（HTC）（4）。 /酮（1），硫代氨基脲（2）和3-（2-溴乙酰基）-2 H-铬-2--2-酮（3）在室温下与环境相容的蒙脱土（MMT）K10粘土催化20–40分钟。当前的MCR策略具有几个优点，包括其广泛的底物范围，生态兼容性，较短的反应时间以及不需要色谱纯化的产品。此外，该方法易于执行，易于构造C–N，C一锅中的N和C–S键可以将反应放大到克级。而且，该催化剂可以重复使用7次而没有明显的活性变化。还研究了合成的D–A型HTC的光物理性质，并注意到荧光性质可以随HTC醛/酮芳环上给电子基团的位置而变化。大多数化合物在氯仿中（1.0×10 -5 M）表现出明亮的荧光，最大发射范围为409至511 nm，斯托克斯位移较大。此外，发现HTC的HOMO和LUMO能级分别在-5
• 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.