3-(2-nitrophenyl)acrylohydrazide | 90349-42-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-nitrophenyl)acrylohydrazide
• 英文别名: o-Nitro-cinnamoyl-hydrazid；3-(2-nitrophenyl)prop-2-enehydrazide
• CAS: 90349-42-1
• 化学式: C₉H₉N₃O₃
• 分子量: 207.189
• InChiKey: FDBZYDSVVLOADI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.26
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(2-nitrophenyl)acrylohydrazide 在 lithium hydride 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 2-(benzylthio)-5-(2-nitrostyryl)-1,3,4-oxadiazole
  参考文献：
  名称：

  SYNTHESIS, STRUCTURAL CHARACTERIZATION AND ENZYME INHIBITION STUDIES ON 5-(2-NITROSTYRYL)-1,3,4-OXADIAZOLE-2-THIOL DERIVATIVES

  摘要：

  In the present work, S-substituted derivatives of 5-(2-nitrostyryl)-1,3,4-oxadiazole-2-thiol (4) were synthesized by successive conversions of 3-(2-nitrophenyl) acrylic acid (1) into its respective ester, hydrazide and 1,3,4-oxadiazole. Finally the target compounds were obtained by reaction of 5-(2-nitrostyryl)-1,3,4-oxadiazole- 2-thiol (4) with a series of various electrophiles, (5a-I), in N, N-dimethyl formamide (DMF) in the presence of sodium hydride (NaH). The structural characterization of these newly synthesized compounds was done by IR, H-1-NMR, HR-MS and EI-MS spectral data. All these compounds were evaluated for their enzyme inhibitory potentials and found to exhibit broad range spectrum against acetylcholinesterase, butyrylcholinestrase and lipoxygenase enzymes.

  DOI：

  10.4067/s0717-97072013000400061
• 作为产物：
  描述：

  2-硝基肉桂酸 在 hydrazine hydrate 、 硫酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 3-(2-nitrophenyl)acrylohydrazide
  参考文献：
  名称：

  SYNTHESIS, STRUCTURAL CHARACTERIZATION AND ENZYME INHIBITION STUDIES ON 5-(2-NITROSTYRYL)-1,3,4-OXADIAZOLE-2-THIOL DERIVATIVES

  摘要：

  In the present work, S-substituted derivatives of 5-(2-nitrostyryl)-1,3,4-oxadiazole-2-thiol (4) were synthesized by successive conversions of 3-(2-nitrophenyl) acrylic acid (1) into its respective ester, hydrazide and 1,3,4-oxadiazole. Finally the target compounds were obtained by reaction of 5-(2-nitrostyryl)-1,3,4-oxadiazole- 2-thiol (4) with a series of various electrophiles, (5a-I), in N, N-dimethyl formamide (DMF) in the presence of sodium hydride (NaH). The structural characterization of these newly synthesized compounds was done by IR, H-1-NMR, HR-MS and EI-MS spectral data. All these compounds were evaluated for their enzyme inhibitory potentials and found to exhibit broad range spectrum against acetylcholinesterase, butyrylcholinestrase and lipoxygenase enzymes.

  DOI：

  10.4067/s0717-97072013000400061