N'-(4-((E)-2-(1-(2-hydroxyethyl)-5-nitro-1H-imidazol-2-yl)vinyl)benzylidene)azepane-1-carbothiohydrazide | 1078662-03-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N'-(4-((E)-2-(1-(2-hydroxyethyl)-5-nitro-1H-imidazol-2-yl)vinyl)benzylidene)azepane-1-carbothiohydrazide
• CAS: 1078662-03-9
• 化学式: C₂₁H₂₆N₆O₃S
• 分子量: 442.542
• InChiKey: FBQSCJPSPMEXOE-WLOZSTFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  108.82
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  azepane-1-carbothioic acid hydrazide 、 2-(4-formylstyryl)-1-(β-hydroxyethyl)-5-nitroimidazole 以 乙醇 为溶剂， 以27%的产率得到N'-(4-((E)-2-(1-(2-hydroxyethyl)-5-nitro-1H-imidazol-2-yl)vinyl)benzylidene)azepane-1-carbothiohydrazide
  参考文献：
  名称：

  Synthesis and antiamoebic activity of metronidazole thiosemicarbazone analogues

  摘要：

  Repeated treatment of Entamoeba histolytica infection with commonly used antiamoebic drugs results in not only increasing the toxicity potential but also leads to the development of clinical resistance. Thus new effective agents with less toxicity against amoebiasis are urgently required. With this view, metronidazole thiosemicarbazone analogues 1-11 were synthesized wherein thioamide moiety was substituted by different cyclic and aromatic amines. These compounds were screened against HMI:IMSS strain of E. histolytica parasite cultured in vitro and the sensitivity of the parasite to the metronidazole thiosemicarbazones was evaluated using the microdilution method. Eight compounds (1-4, 7-9 and 11) were found better inhibitors of E. histolytica growth since IC50 values elicited by these compounds were much lower than metronidazole with compound 4 showing the most promising antiamoebic activity (IC50 = 0.56 mu M). The study suggests the beneficial potential of these leads that need to be further explored in order to discover and develop better and yet safer therapeutic agents for amoebiasis. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.12.007