(E)‑3‑(2‑(2‑(3‑methoxybenzylidene)hydrazinyl)thiazol‑4‑yl)‑2H‑chromen‑2‑one | 1408315-95-6

• 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‑(3‑methoxybenzylidene)hydrazinyl)thiazol‑4‑yl)‑2H‑chromen‑2‑one
• 英文别名: (e)-3-(2-(2-(3-Methoxybenzylidene)hydrazinyl)thiazol-4-yl)-2h-chromen-2-one；3-[2-[(2E)-2-[(3-methoxyphenyl)methylidene]hydrazinyl]-1,3-thiazol-4-yl]chromen-2-one
• CAS: 1408315-95-6
• 化学式: C₂₀H₁₅N₃O₃S
• 分子量: 377.423
• InChiKey: LQWBRJZLRPHBOL-SRZZPIQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-乙酰基香豆素 在 溴 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 (E)‑3‑(2‑(2‑(3‑methoxybenzylidene)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

• Aryl hydrazones linked thiazolyl coumarin hybrids as potential urease inhibitors
  作者：Uzma Salar、Bakhtawer Qureshi、Khalid Mohammed Khan、Muhammad Arif Lodhi、Zaheer Ul‑Haq、Farman Ali Khan、Fouzia Naz、Muhammad Taha、Shahnaz Perveen、Shafqat Hussain

  DOI：10.1007/s13738-021-02377-8

  日期：2022.4

  Aryl hydrazones bearing thiazolyl coumarin hybrids 1–32 were prepared by following 'one-pot' two-steps reaction scheme. Various arylaldehydes were reacted to thiosemicarbazide under acidic condition to form aryl thiosemicarbazone intermediates which in turn treated with 3-bromoacetyl coumarin under basic condition to afford thiazolyl coumarin hybrids 1–32. All hybrids were recognized by EI- and HREI-MS

  通过遵循“一锅”两步反应方案制备带有噻唑基香豆素杂化物1-32的芳基腙。各种芳醛在酸性条件下与氨基硫脲反应形成芳基氨基氨基硫脲中间体，该中间体又在碱性条件下用 3-溴乙酰香豆素处理，得到噻唑基香豆素杂化物 1-32。所有杂种均通过 EI-和 HREI-MS 以及 1H-和 13C-NMR 光谱技术进行识别。筛选化合物 1-32 对脲酶的体外抑制活性，并在 IC50 = 16.29 ± 1.1-256.30 ± 1.4 µM 范围内显示出良好至中等的抑制潜力。值得指出的是，化合物 21 (IC50 = 16.29 ± 1.1 µM) 被确定为比标准乙酰氧肟酸 (IC50 = 27.0 ± 0.5 µM) 更有效的脲酶抑制剂。衍生物 19 (IC50 = 77.67 ± 1. 5 µM) 和 30 (IC50 = 71.21 ± 1.6 µM) 被发现具有中度活性。构效关系表明-F、-Cl、-
• 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.