5-Nitro-2-furaldehyde 4-(3-(diethylamino)propyl)semicarbazone | 101858-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-Nitro-2-furaldehyde 4-(3-(diethylamino)propyl)semicarbazone
• 英文别名: 1-[3-(diethylamino)propyl]-3-[(E)-(5-nitrofuran-2-yl)methylideneamino]urea
• CAS: 101858-16-6
• 化学式: C₁₃H₂₁N₅O₄
• 分子量: 311.341
• InChiKey: PCJJYLQECJTKOW-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-硝基糠醛 、 N₄-<3-(diethylamino)propyl>semicarbazide 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 以48%的产率得到5-Nitro-2-furaldehyde 4-(3-(diethylamino)propyl)semicarbazone
  参考文献：
  名称：

  Synthesis and antitrypanosomal evaluation of E-isomers of 5-nitro-2-furaldehyde and 5-nitrothiophene-2-carboxaldehyde semicarbazone derivatives. Structure–activity relationships.

  摘要：

  Several novel semicarbazone derivatives were prepared from 5-nitro-2-furaldehyde or 5-nitrothiophene-2-carboxaldehyde and semicarbazides bearing a spermidine-mimetic moiety. All derivatives presented the E-configuration, as determined by NMR-NOE experiments. These compounds were tested in vitro as potential antitrypanosomal agents, and some of them, together with the parent compounds, 5-nitro-2-furaldehyde and 5-nitrothiophene-2-carboxaldehyde semicarbazone derivatives, were also evaluated in vivo using infected mice. Structure-activity relationship studies were carried out using voltammetric response and lipophilic-hydrophilic balance as parameters. Two of the compounds (1 and 3) displayed the highest in vivo activity. A correlation was found between lipophilic-hydrophilic properties and trypanocidal activity, high R-M values being associated with low in vivo effects. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00131-8

文献信息

• Synthesis and antitrypanosomal evaluation of E-isomers of 5-nitro-2-furaldehyde and 5-nitrothiophene-2-carboxaldehyde semicarbazone derivatives. Structure–activity relationships.
  作者：H Cerecetto

  DOI：10.1016/s0223-5234(00)00131-8

  日期：2000.3

  Several novel semicarbazone derivatives were prepared from 5-nitro-2-furaldehyde or 5-nitrothiophene-2-carboxaldehyde and semicarbazides bearing a spermidine-mimetic moiety. All derivatives presented the E-configuration, as determined by NMR-NOE experiments. These compounds were tested in vitro as potential antitrypanosomal agents, and some of them, together with the parent compounds, 5-nitro-2-furaldehyde and 5-nitrothiophene-2-carboxaldehyde semicarbazone derivatives, were also evaluated in vivo using infected mice. Structure-activity relationship studies were carried out using voltammetric response and lipophilic-hydrophilic balance as parameters. Two of the compounds (1 and 3) displayed the highest in vivo activity. A correlation was found between lipophilic-hydrophilic properties and trypanocidal activity, high R-M values being associated with low in vivo effects. (C) 2000 Editions scientifiques et medicales Elsevier SAS.