4-(1H-imidazole-1-yl)-benzaldehyde-benzoylhydrazone | 1609163-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(1H-imidazole-1-yl)-benzaldehyde-benzoylhydrazone
• 英文别名: N-[(E)-(4-imidazol-1-ylphenyl)methyleneamino]benzamide；N-[(E)-(4-imidazol-1-ylphenyl)methylideneamino]benzamide
• CAS: 1609163-03-2
• 化学式: C₁₇H₁₄N₄O
• 分子量: 290.324
• InChiKey: AFNKHUDUXXGRDX-XDHOZWIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲酰肼 、 1-(4-甲醛基苯基)咪唑 以 甲醇 为溶剂， 反应 6.0h， 以84%的产率得到4-(1H-imidazole-1-yl)-benzaldehyde-benzoylhydrazone
  参考文献：
  名称：

  Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi

  摘要：

  通过4(5)-咪唑甲醛、4-(1H-咪唑-1-基)苯甲醛和4-(1H-咪唑-1-基)乙酰苯与硫代半卡巴肼或酰肼的缩合反应，合成了新的咪唑衍生的硫代半卡巴脘和脘。所有化合物均通过定量元素分析、红外和核磁共振技术进行了表征。通过单晶X射线衍射确定了八种结构。评估了这些化合物的抗真菌活性。这些化合物对黄曲霉和白色念珠菌均无显著活性，而4(5)-咪唑甲醛硫代半卡巴脘（ImT）和4-(1H-咪唑-1-基)苯甲醛硫代半卡巴脘（4ImBzT）对枝孢枝孢菌表现出了高度且选择性的活性。4(5)-咪唑甲醛苯甲酰脘（4(5)ImPh）、4(5)-咪唑甲醛对氯苯甲酰脘（4(5)ImpClPh）、4(5)-咪唑甲醛对硝基苯甲酰脘（4(5)ImpNO2Ph）、4-(咪唑-1-基)乙酰苯对氯苯甲酰脘（4ImAcpClPh）和4-(咪唑-1-基)乙酰苯对硝基苯甲酰脘（4ImAcpNO2Ph）对光滑念珠菌表现出了高度活性。4(5)ImpClPh和4(5)ImpNO2Ph对枝孢枝孢菌非常有效。在许多情况下，活性优于参考化合物制霉菌素。

  DOI：

  10.3390/molecules181012645

文献信息

• Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi
  作者：Débora Reis、Angel Despaigne、Jeferson Silva、Nayane Silva、Camila Vilela、Isolda Mendes、Jacqueline Takahashi、Heloisa Beraldo

  DOI：10.3390/molecules181012645

  日期：——

  New imidazole derived thiosemicarbazones and hydrazones were prepared by condensation of 4(5)-imidazole carboxaldehyde, 4-(1H-imidazole-1-yl)benzaldehyde and 4-(1H-imidazole-1-yl)acetophenone with a thiosemicarbazide or hydrazide. All compounds were characterized by quantitative elemental analysis, IR and NMR techniques. Eight structures were determined by single crystal X-ray diffraction. The antifungal activities of the compounds were evaluated. None of the compounds exhibited significant activity against Aspergillus flavus and Candida albicans, while 4(5)-imidazolecarboxaldehyde thiosemicarbazone (ImT) and 4-(1H-imidazole-1-yl)benzaldehyde thiosemicabazone (4ImBzT) were highly and selectively active against Cladosporium cladosporioides. 4(5)-Imidazolecarboxaldehyde benzoyl hydrazone (4(5)ImPh), 4(5)-imidazolecarboxaldehyde-para-chlorobenzoyl hydrazone (4(5)ImpClPh), 4(5)-imidazolecarboxaldehyde-para-nitrobenzoyl hydrazone (4(5)ImpNO2Ph), 4-(imidazole-1-yl)acetophenone-para-chloro-benzoyl hydrazone (4ImAcpClPh) and 4-(imidazole-1-yl)acetophenone-para-nitro-benzoylhydrazone (4ImAcpNO2Ph) were highly active against Candida glabrata. 4(5)ImpClPh and 4(5)ImpNO2Ph were very effective against C. cladosporioides. In many cases, activity was superior to that of the reference compound nystatin.

  通过4(5)-咪唑甲醛、4-(1H-咪唑-1-基)苯甲醛和4-(1H-咪唑-1-基)乙酰苯与硫代半卡巴肼或酰肼的缩合反应，合成了新的咪唑衍生的硫代半卡巴脘和脘。所有化合物均通过定量元素分析、红外和核磁共振技术进行了表征。通过单晶X射线衍射确定了八种结构。评估了这些化合物的抗真菌活性。这些化合物对黄曲霉和白色念珠菌均无显著活性，而4(5)-咪唑甲醛硫代半卡巴脘（ImT）和4-(1H-咪唑-1-基)苯甲醛硫代半卡巴脘（4ImBzT）对枝孢枝孢菌表现出了高度且选择性的活性。4(5)-咪唑甲醛苯甲酰脘（4(5)ImPh）、4(5)-咪唑甲醛对氯苯甲酰脘（4(5)ImpClPh）、4(5)-咪唑甲醛对硝基苯甲酰脘（4(5)ImpNO2Ph）、4-(咪唑-1-基)乙酰苯对氯苯甲酰脘（4ImAcpClPh）和4-(咪唑-1-基)乙酰苯对硝基苯甲酰脘（4ImAcpNO2Ph）对光滑念珠菌表现出了高度活性。4(5)ImpClPh和4(5)ImpNO2Ph对枝孢枝孢菌非常有效。在许多情况下，活性优于参考化合物制霉菌素。