4-phenylazo-2-hydroxybenzaldehyde | 56288-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4-phenylazo-2-hydroxybenzaldehyde
• 英文别名: 4-benzeneazosalicylaldehyde；p-Phenylazo-salicylaldehyde；2-hydroxy-4-phenyldiazenylbenzaldehyde
• CAS: 56288-70-1
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: BHHZZXHTGCPYQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 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：
  62
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  异烟肼 、 4-phenylazo-2-hydroxybenzaldehyde 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以85%的产率得到
  参考文献：
  名称：

  结构简单的基于偶氮基的生色R1用于选择性检测水性介质中的氰化物离子

  摘要：

  合成了结构简单的偶氮连接的席夫碱R1，并使用IR，1 H NMR和质谱技术对其进行了表征。肉眼颜色变化和紫外可见光谱揭示了氰化物阴离子对其他阴离子如氟离子，氯离子，溴离子，碘离子，乙酸根，硝酸根，硫酸氢根和磷酸二氢根的选择性感测。CN的加成-离子向R1显示在颜色了戏剧性的变化从与在415nm处，即使在100％的水性介质的形成一个新的条带中的吸收光谱沿淡黄色至强烈的黄色。还使用1 H NMR滴定研究了R1和氰化物之间的相互作用。该R1在2.72×10检测（LOD）达到微摩尔水平的显示极限- 6  M.工作的图揭示的现有装订模式R1和CN -在1摩尔比的离子：1（R1：CN - ）。

  DOI：

  10.1016/j.saa.2016.07.045

文献信息

• Colorimetric recognition of acetate anions in aqueous solution using charge neutral azo derivatives
  作者：Weiwei Huang、Yaping Li、Hai Lin、Huakuan Lin

  DOI：10.1016/j.saa.2011.10.064

  日期：2012.2

  Two novel highly sensitive colorimetric acetate anion receptors: 4-phenylazo-2-hydroxy-benzaldehyde 4-nitrophenylhydrazone (1) and 4-phenylazo-2-hydroxy-benzaldehyde 2,4-dinitrophenylhydrazone (2) based on azo derivative have been designed and synthesized. UV-vis experiments show that receptor 1 and receptor 2 can selectively recognize acetate in DMSO and even in 9/1 DMSO/H(2)O (v/v) mixtures. Meanwhile

  设计了两种新型的高灵敏度比色乙酸根阴离子受体：基于偶氮衍生物的4-苯基偶氮-2-羟基苯甲醛4-硝基苯hydr（1）和4-苯基偶氮-2-羟基苯甲醛2,4-二硝基苯hydr（2），并合成的。紫外可见实验表明，受体1和受体2可以选择性地识别DMSO中的乙酸盐，甚至9/1 DMSO / H（2）O（v / v）混合物中的乙酸盐。同时，由阴离子引起的颜色变化可以提供一种“裸眼”检测的方法。通过（1）H NMR滴定实验研究了受体1、2与AcO（-）之间相互作用的性质的进一步见解。
• Design, green one-pot synthesis and molecular docking study of novel N,N-bis(cyanoacetyl)hydrazines and bis-coumarins as effective inhibitors of DNA gyrase and topoisomerase IV
  作者：Nadia Hanafy Metwally、Sanaa Osman Abdallah、Marwa Maher Abdel Mohsen

  DOI：10.1016/j.bioorg.2020.103672

  日期：2020.4

  A novel, quick, environmentally safe, and one-pot synthesis of a series of N,N-bis(cyanoacetyl)hydrazine derivatives, bis-imino-2H-chromenes and bis-2-oxo-2H-chromene derivatives have been designed. Some selected newly synthesized compounds were investigated in vitro for their antibacterial activity. Compound 5j is the most toxic compound against Staphylococcus aureus with activity index 171%, followed by compound 15b with activity index 136% compared to standard drug ampicillin. Moreover, compound 15a is the most toxic compound against Escherichia coli with activity index 111% compared to standard drug gentamicin. Minimum inhibitory concentration (MIC) was carried out for compounds with high antibacterial activity. Compound 5j has good MIC (7.8 mu g/ml) against Staphylococcus aureus while 15a has good MIC (31.25 mu g/ml) against Streptococcus mutans which is better than MIC of the standard drug ampicillin (MIC = 62.5 mu g/ml). Compounds 5j, 5k, 15a, 15b and 15e which have good MIC values were introduced to enzyme assay against DNA gyrase and topoisomerase IV. The results showed that compound 15a can strongly inhibit DNA gyrase and topoisomerase IV (IC50 = 27.30 and 25.52 mu M respectively), compared to methotrexate as the standard drug (IC50 = 29.01 and 23.55 mu M respectively). Structure-activity relationships were also discussed based on the biological and docking simulation results.