1-ethyl-3-[(E)-(5-nitrofuran-2-yl)methylideneamino]thiourea

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 1-ethyl-3-[(E)-(5-nitrofuran-2-yl)methylideneamino]thiourea
• 化学式: C₈H₁₀N₄O₃S
• 分子量: 242.258
• InChiKey: UIEWYHUUSJLKRI-BJMVGYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-硝基糠醛 、 4-乙基-3-硫代氨基脲 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以89%的产率得到1-ethyl-3-[(E)-(5-nitrofuran-2-yl)methylideneamino]thiourea
  参考文献：
  名称：

  In vitro activity and mechanism of action against the protozoan parasite Trypanosoma cruzi of 5-nitrofuryl containing thiosemicarbazones

  摘要：

  The in vitro growth inhibition activity of new thiosemicarbazone derivatives against the protozoan parasite Trypanosoma cruzi, the causative agent of American trypanosomiasis, are described. The designed compounds combine in the same molecule the thiosemicarbazone function, recently described as a potent cruzain-inhibitor moiety, and the recognised 5-nitrofuryl group, an oxidative stress promoter. Some of the derivatives were found to be very active against the cultured (epimastigote) form of the parasite, being 1.5-1.7-fold more active than the reference compound, Nifurtimox. Free radicals production was detected when the compounds were incubated in presence of mammalian-liver microsomes. The thiosemicarbazones' capacity to act as pharmacophore in the cruzain inhibition process was theoretically analysed. Frontier molecular orbital HOMO was found as an adequate descriptor in this process. Acute in vivo toxicity of two of the more active derivatives was evaluated. The results showed that these compounds are among the most potent 5-nitrofuryl derivatives tested against this parasite thus support further in vivo studies of some of these thiosemicarbazones. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.003

文献信息

• Thiosemicarbazones active against Clostridium difficile
  作者：Cait Costello、Tarja Karpanen、Peter A. Lambert、Preena Mistry、Katy J. Parker、Daniel L. Rathbone、Jiangmeng Ren、Laura Wheeldon、Tony Worthington

  DOI：10.1016/j.bmcl.2008.01.041

  日期：2008.3

  A set of closely related furylidene thiosemicarbazones was prepared and screened against various clinically important Gram-positive bacteria. One compound containing an ethylene spacer and a 5-nitrofuryl group was found to have promising activity against Clostridium difficile. (C) 2008 Elsevier Ltd. All rights reserved.