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

• 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-[(E)-(5-nitrofuran-2-yl)methylideneamino]-3-phenylthiourea
• 化学式: C₁₂H₁₀N₄O₃S
• 分子量: 290.302
• InChiKey: CUHPRPSWISMFMH-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(E)-(5-nitrofuran-2-yl)methylideneamino]-3-phenylthiourea 、 三氯化铁 以85%的产率得到
  参考文献：
  名称：

  MARTVON A.; STANKOVSKY S.; UHER M., CHEM. 2VESTI, 1980, 34, NO 1, 118-124

  摘要：

  DOI：
• 作为产物：
  描述：

  5-硝基糠醛 、 4-苯基-3-硫代氨基脲 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以80%的产率得到1-[(E)-(5-nitrofuran-2-yl)methylideneamino]-3-phenylthiourea
  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