(E)-N'-((furan-2-yl)methylene)azepane-1-carbothiohydrazide | 1253912-91-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: (E)-N'-((furan-2-yl)methylene)azepane-1-carbothiohydrazide
• 英文别名: N-[(E)-furan-2-ylmethylideneamino]azepane-1-carbothioamide
• CAS: 1253912-91-2
• 化学式: C₁₂H₁₇N₃OS
• 分子量: 251.352
• InChiKey: DYTWGLFSHGAPHM-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  糠醛 、 azepane-1-carbothioic acid hydrazide 在 水 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 (E)-N'-((furan-2-yl)methylene)azepane-1-carbothiohydrazide
  参考文献：
  名称：

  Structure–activity relationships of mononuclear metal–thiosemicarbazone complexes endowed with potent antiplasmodial and antiamoebic activities

  摘要：

  A useful concept for the rational design of antiparasitic drug candidates is the complexation of bioactive ligands with transition metals. In view of this, an investigation was conducted into a new set of metal complexes as potential antiplasmodium and antiamoebic agents, in order to examine the importance of metallic atoms, as well as the kind of sphere of co-ordination, in these biological properties. Four functionalized furyl-thiosemicarbazones (NT1-4) treated with divalent metals (Cu, Co, Pt, and Pd) to form the mononuclear metallic complexes of formula [M(L)(2)Cl-2] or [M(L)Cl-2] were examined. The pharmacological characterization, including assays against Plasmodium falciparum and Entamoeba histolytica, cytotoxicity to mammalian cells, and interaction with pBR 322 plasmid DNA was performed. Structure-activity relationship data revealed that the metallic complexation plays an essential role in antiprotozoal activity, rather than the simple presence of the ligand or metal alone. Important steps towards identification of novel antiplasmodium (NT1Cu, IC50 of 4.6 mu M) and antiamoebic (NT2Pd, IC50 of 0.6 mu M) drug prototypes were achieved. Of particular relevance to this work, these prototypes were able to reduce the proliferation of these parasites at concentrations that are not cytotoxic to mammalian cells. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.07.039

文献信息

• Structure–activity relationships of mononuclear metal–thiosemicarbazone complexes endowed with potent antiplasmodial and antiamoebic activities
  作者：Deepa Bahl、Fareeda Athar、Milena Botelho Pereira Soares、Matheus Santos de Sá、Diogo Rodrigo Magalhães Moreira、Rajendra Mohan Srivastava、Ana Cristina Lima Leite、Amir Azam

  DOI：10.1016/j.bmc.2010.07.039

  日期：2010.9

  A useful concept for the rational design of antiparasitic drug candidates is the complexation of bioactive ligands with transition metals. In view of this, an investigation was conducted into a new set of metal complexes as potential antiplasmodium and antiamoebic agents, in order to examine the importance of metallic atoms, as well as the kind of sphere of co-ordination, in these biological properties. Four functionalized furyl-thiosemicarbazones (NT1-4) treated with divalent metals (Cu, Co, Pt, and Pd) to form the mononuclear metallic complexes of formula [M(L)(2)Cl-2] or [M(L)Cl-2] were examined. The pharmacological characterization, including assays against Plasmodium falciparum and Entamoeba histolytica, cytotoxicity to mammalian cells, and interaction with pBR 322 plasmid DNA was performed. Structure-activity relationship data revealed that the metallic complexation plays an essential role in antiprotozoal activity, rather than the simple presence of the ligand or metal alone. Important steps towards identification of novel antiplasmodium (NT1Cu, IC50 of 4.6 mu M) and antiamoebic (NT2Pd, IC50 of 0.6 mu M) drug prototypes were achieved. Of particular relevance to this work, these prototypes were able to reduce the proliferation of these parasites at concentrations that are not cytotoxic to mammalian cells. (C) 2010 Published by Elsevier Ltd.