2-[(4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl]-N-(4-fluorophenyl) hydrazinecarbothioamide | 1491159-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-[(4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl]-N-(4-fluorophenyl) hydrazinecarbothioamide
• 英文别名: 1-[(4,6-dioxo-2-sulfanylidene-1,3-diazinan-5-ylidene)methylamino]-3-(4-fluorophenyl)thiourea
• CAS: 1491159-61-5
• 化学式: C₁₂H₁₀FN₅O₂S₂
• 分子量: 339.374
• InChiKey: QAZQHVMRLODQDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.03
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.29
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  4,6-二羟基-2-巯基嘧啶 、 4-(4-氟苯)-3-氨基硫脲 、 原甲酸三乙酯 以 仲丁醇 为溶剂， 反应 3.0h， 以92%的产率得到2-[(4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl]-N-(4-fluorophenyl) hydrazinecarbothioamide
  参考文献：
  名称：

  Synthesis, molecular docking studies, and in vitro screening of barbiturates/thiobarbiturates as antibacterial and cholinesterase inhibitors

  摘要：

  On the basis of observed biological activity of barbiturates/thiobarbiturates, a set of 13 hydrazinecarboxamide/hydrazinecarbothioamides derivatives were designed and synthesized in good to excellent yield with extensive structural characterization. These compounds were screened for antibacterial and cholinesterase inhibitory activities. Two of the compounds 1 and 2 showed moderate bactericidal activity. Compounds 10 and 4 were found to be the most active acetyl/butyryl cholinesterase inhibitor, respectively (AChEI; 10; IC50 = 40.78 mu M and BChEI; 4; IC50 = 3.31 mu M). In silico molecular docking studies were carried out to identify active interacting sites of drug and enzyme and to establish structure-activity relationships. When predicted cholinesterase binding energies were compared with the experimentally determined inhibitory concentrations (IC50), most active compounds were also found to be the most favorable for binding. The binding scores of compounds 10 and 4 were -10.2 and -9.3 kcal/mol, respectively.

  DOI：

  10.1007/s00044-013-0847-2

文献信息

• Synthesis, molecular docking studies, and in vitro screening of barbiturates/thiobarbiturates as antibacterial and cholinesterase inhibitors
  作者：Saira Mumtaz、Rashad Hussain、Abdul Rauf、M. Q. Fatmi、H. Bokhari、M. Oelgemöller、A. M. Qureshi

  DOI：10.1007/s00044-013-0847-2

  日期：2014.6

  On the basis of observed biological activity of barbiturates/thiobarbiturates, a set of 13 hydrazinecarboxamide/hydrazinecarbothioamides derivatives were designed and synthesized in good to excellent yield with extensive structural characterization. These compounds were screened for antibacterial and cholinesterase inhibitory activities. Two of the compounds 1 and 2 showed moderate bactericidal activity. Compounds 10 and 4 were found to be the most active acetyl/butyryl cholinesterase inhibitor, respectively (AChEI; 10; IC50 = 40.78 mu M and BChEI; 4; IC50 = 3.31 mu M). In silico molecular docking studies were carried out to identify active interacting sites of drug and enzyme and to establish structure-activity relationships. When predicted cholinesterase binding energies were compared with the experimentally determined inhibitory concentrations (IC50), most active compounds were also found to be the most favorable for binding. The binding scores of compounds 10 and 4 were -10.2 and -9.3 kcal/mol, respectively.