4-Methoxybenzaldehyd-4-fluorbenzoylhydrazon | 62433-19-6

• 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: 4-Methoxybenzaldehyd-4-fluorbenzoylhydrazon
• 英文别名: 4-fluoro-N-[(4-methoxyphenyl)methylideneamino]benzamide
• CAS: 62433-19-6
• 化学式: C₁₅H₁₃FN₂O₂
• 分子量: 272.279
• InChiKey: NRVCEWCBJQQNPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Methoxybenzaldehyd-4-fluorbenzoylhydrazon 、 乙酸酐 反应 2.0h， 以85%的产率得到3-acetyl-5-(4-fluorophenyl)-2-(4-methoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and biological activity of hydrazide–hydrazones and their corresponding 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles

  摘要：

  Various 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles (11-20) were prepared by the reaction of aryl substituted hydrazones of 4-fluorobenzoic acid hydrazide (1-10) with acetic anhydride. The structures of the synthesized compounds 11-20, were confirmed by UV, IR, H-1-NMR and mass spectroscopic methods. Antifungal evaluation of the hydrazide-hydrazones 1-10 and corresponding 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles 11-20, against clinical and standard Candida pathogens have been performed by using agar diffusion to indentify the active compounds, which were later subjected to a broth microdilution assay to justify the activity level in terms of minimum inhibitory concentrations (MIC). 4-Fluorobenzoic acid [(5-bromothiophen-2-yl)methylene]hydrazide, showed the highest inhibitory activity against Candida albicans (MIC: 125 mu g/ml), and when compared with ketoconazole. In addition, bioauthographic antifungal activity against plant pathogenic fungi such as Colletotrichum, Botrytis, Fusarium, and Phomopsis was conducted. 4-Fluorobenzoic acid [(5-bromothiophen-2-yl)methylene]hydrazide was the most active analog against P. viticola with 91% inhibition at 30 mu M after 144 h. Furthermore, known and the newly synthesized compounds were also screened through a panel of bioassays to determine their anti-inflammatory, cytotoxic, and antioxidant activities in mammalian cells. 3-Acetyl-5-(4-fluorophenyl)-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole, showed a strong inhibition of NF-kappa B-dependent transcription in SW1353 cells with IC50 value of 0.75 mu g/ml. 4-Fluorobenzoic acid [(3-hydroxy-4-methoxyphenyl)methylene]hydrazide, and 3-acetyl-5-(4-fluorophenyl)-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole on intracellular ROS generation in PMA induced HL-60 cells demonstrated potent activity with IC50 values of 0.9 mu g/ml. A strong inhibition of the activity of iNOS activity in LPS induced RAW 264.7 cells was observed for 3-acetyl-5-(4-fluorophenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1,3,4-oxadiazole with IC50 value of 0.3 mu g/ml.

  DOI：

  10.1007/s00044-011-9882-z
• 作为产物：
  描述：

  4-氟苯甲酰肼 、 4-甲氧基苯甲醛 以 乙醇 为溶剂， 生成 4-Methoxybenzaldehyd-4-fluorbenzoylhydrazon
  参考文献：
  名称：

  Synthesis and biological activity of hydrazide–hydrazones and their corresponding 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles

  摘要：

  Various 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles (11-20) were prepared by the reaction of aryl substituted hydrazones of 4-fluorobenzoic acid hydrazide (1-10) with acetic anhydride. The structures of the synthesized compounds 11-20, were confirmed by UV, IR, H-1-NMR and mass spectroscopic methods. Antifungal evaluation of the hydrazide-hydrazones 1-10 and corresponding 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles 11-20, against clinical and standard Candida pathogens have been performed by using agar diffusion to indentify the active compounds, which were later subjected to a broth microdilution assay to justify the activity level in terms of minimum inhibitory concentrations (MIC). 4-Fluorobenzoic acid [(5-bromothiophen-2-yl)methylene]hydrazide, showed the highest inhibitory activity against Candida albicans (MIC: 125 mu g/ml), and when compared with ketoconazole. In addition, bioauthographic antifungal activity against plant pathogenic fungi such as Colletotrichum, Botrytis, Fusarium, and Phomopsis was conducted. 4-Fluorobenzoic acid [(5-bromothiophen-2-yl)methylene]hydrazide was the most active analog against P. viticola with 91% inhibition at 30 mu M after 144 h. Furthermore, known and the newly synthesized compounds were also screened through a panel of bioassays to determine their anti-inflammatory, cytotoxic, and antioxidant activities in mammalian cells. 3-Acetyl-5-(4-fluorophenyl)-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole, showed a strong inhibition of NF-kappa B-dependent transcription in SW1353 cells with IC50 value of 0.75 mu g/ml. 4-Fluorobenzoic acid [(3-hydroxy-4-methoxyphenyl)methylene]hydrazide, and 3-acetyl-5-(4-fluorophenyl)-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole on intracellular ROS generation in PMA induced HL-60 cells demonstrated potent activity with IC50 values of 0.9 mu g/ml. A strong inhibition of the activity of iNOS activity in LPS induced RAW 264.7 cells was observed for 3-acetyl-5-(4-fluorophenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1,3,4-oxadiazole with IC50 value of 0.3 mu g/ml.

  DOI：

  10.1007/s00044-011-9882-z

文献信息

• Thermo-Induced Fluorochromism in Two AIE Zinc Complexes: A Deep Insight into the Structure-Property Relationship
  作者：Rosita Diana、Ugo Caruso、Francesco Silvio Gentile、Luigi Di Costanzo、Pellegrino Musto、Barbara Panunzi

  DOI：10.3390/molecules27082551

  日期：——

  solid-state emissive coordination complexes offer a variety of fluorescence responses related to the dynamic of noncovalent metal-ligand coordination bonds. Relevant FC behaviour can result from the targeted choice of metal cation and ligands. Herein, we report the synthesis and characterization of two different colour emitters consisting of zinc complexes obtained from N,O bidentate ligands with different

  表现出机械荧光变色或热荧光变色响应的固态发射器代表了用于新技术应用的智能工具的基础。在荧光变色 (FC) 材料中，固态发光配位配合物提供多种与非共价金属-配体配位键的动态相关的荧光响应。相关的 FC 行为可能来自金属阳离子和配体的目标选择。在这里，我们报告了两种不同颜色的发光体的合成和表征，这些发光体由从N、O获得的锌配合物组成。具有不同吸电子取代基的双齿配体。这两种复合物分别是蓝色和橙色固态荧光团，对热应力和机械应力高度敏感。这些发射器在退火处理之前和之后显示出非常不同的光致发光 (PL) 图案。通过 X 射线结构分析与热分析、红外 (IR) 光谱、PL 和 DFT 模拟相结合，我们对荧光变色响应中涉及的结构特征进行了全面分析。值得注意的是，我们能够将配合物的开关热荧光变色与锌配位核心的结构重排联系起来。
• Synthesis and biological activity of hydrazide–hydrazones and their corresponding 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles
  作者：Bedia Koçyiğit-Kaymakçıoğlu、Emine Elçin Oruç-Emre、Seda Ünsalan、Nurhayat Tabanca、Shabana Iqrar Khan、David Earl Wedge、Gökalp İşcan、Fatih Demirci、Sevim Rollas

  DOI：10.1007/s00044-011-9882-z

  日期：2012.11

  Various 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles (11-20) were prepared by the reaction of aryl substituted hydrazones of 4-fluorobenzoic acid hydrazide (1-10) with acetic anhydride. The structures of the synthesized compounds 11-20, were confirmed by UV, IR, H-1-NMR and mass spectroscopic methods. Antifungal evaluation of the hydrazide-hydrazones 1-10 and corresponding 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles 11-20, against clinical and standard Candida pathogens have been performed by using agar diffusion to indentify the active compounds, which were later subjected to a broth microdilution assay to justify the activity level in terms of minimum inhibitory concentrations (MIC). 4-Fluorobenzoic acid [(5-bromothiophen-2-yl)methylene]hydrazide, showed the highest inhibitory activity against Candida albicans (MIC: 125 mu g/ml), and when compared with ketoconazole. In addition, bioauthographic antifungal activity against plant pathogenic fungi such as Colletotrichum, Botrytis, Fusarium, and Phomopsis was conducted. 4-Fluorobenzoic acid [(5-bromothiophen-2-yl)methylene]hydrazide was the most active analog against P. viticola with 91% inhibition at 30 mu M after 144 h. Furthermore, known and the newly synthesized compounds were also screened through a panel of bioassays to determine their anti-inflammatory, cytotoxic, and antioxidant activities in mammalian cells. 3-Acetyl-5-(4-fluorophenyl)-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole, showed a strong inhibition of NF-kappa B-dependent transcription in SW1353 cells with IC50 value of 0.75 mu g/ml. 4-Fluorobenzoic acid [(3-hydroxy-4-methoxyphenyl)methylene]hydrazide, and 3-acetyl-5-(4-fluorophenyl)-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole on intracellular ROS generation in PMA induced HL-60 cells demonstrated potent activity with IC50 values of 0.9 mu g/ml. A strong inhibition of the activity of iNOS activity in LPS induced RAW 264.7 cells was observed for 3-acetyl-5-(4-fluorophenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1,3,4-oxadiazole with IC50 value of 0.3 mu g/ml.