1-(3-formyl-4-hydroxyphenylazo)-4-chloro-3-nitrobenzene | 1367182-07-7

• 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: 1-(3-formyl-4-hydroxyphenylazo)-4-chloro-3-nitrobenzene
• 英文别名: 5-[(4-Chloro-3-nitrophenyl)diazenyl]-2-hydroxybenzaldehyde
• CAS: 1367182-07-7
• 化学式: C₁₃H₈ClN₃O₄
• 分子量: 305.677
• InChiKey: ASDXGDWSOMOXOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 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：
  108
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3-formyl-4-hydroxyphenylazo)-4-chloro-3-nitrobenzene 、 二甘醇胺 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以32%的产率得到1-{3-[(2-hydroxyethoxyethylimino)methyl]-4-hydroxyphenylazo}-4-chloro-3-nitrobenzene
  参考文献：
  名称：

  Synthesis and studies of selective chemosensors for anions and cations by azo-containing salicylaldimine-based receptors

  摘要：

  Three new chromogenic receptors containing electron-withdrawing groups appended to the azophenol moiety were synthesized, characterized, and their chromogenic behavior toward various anions and cations investigated. These chemosensors show visual changes towards biologically relevant anions like F and OH, and also towards various cations such as Cu2+, Co2+, Ni2+, Mn2+, and Zn2+. Yet, other anions such as Cl, Br, and NO3 could not cause any color change. The sensing action was further confirmed by UVVis titration. 1H-NMR experiments were carried out to explore the nature of interaction between receptors with F and OH. The binding constants (K a) of the hostguest complexes formed were determined.

  DOI：

  10.1080/00958972.2012.752818
• 作为产物：
  描述：

  3-硝基-4-氯苯胺 、 水杨醛 在 盐酸 、 sodium carbonate 、 sodium hydroxide 、 sodium nitrite 作用下， 以 水 为溶剂， 以78%的产率得到1-(3-formyl-4-hydroxyphenylazo)-4-chloro-3-nitrobenzene
  参考文献：
  名称：

  The Coumarin Psoralidin Enhances Anticancer Effect of Tumor Necrosis Factor-Related Apoptosis-Inducing Ligand (TRAIL)

  摘要：

  香豆素是一类非常常见的次级植物代谢物，具有广泛的生物活性。普拉利定是一种天然存在的呋喃香豆素，来自小豆蔻（Psoralea corylifolia），具有抗癌和化学预防特性。肿瘤坏死因子相关凋亡诱导配体（TRAIL）能够诱导癌细胞 apoptosis，而对正常组织无毒性。内源性TRAIL在免疫监视和防御癌细胞方面发挥着重要作用。香豆素可以调节癌细胞中TRAIL介导的凋亡。我们研究了普拉利定与TRAIL联合对HeLa癌细胞的细胞毒性和凋亡活性。通过MTT和LDH检测其细胞毒性。采用annexin V-FITC染色法检测凋亡，使用DePsipher染色法通过荧光显微镜评估线粒体膜电位。死受体（TRAIL-R1/DR4和TRAIL-R2/DR5）的表达通过流式细胞术进行分析。普拉利定通过增加TRAIL-R2死受体的表达和线粒体膜电位去极化，增强了HeLa细胞中TRAIL诱导的凋亡。我们的研究表明，普拉利定增强了TRAIL的抗癌效果，确认了香豆素在癌症化学预防中的潜在应用。

  DOI：

  10.3390/molecules17066449

文献信息

• Synthesis and Biological Activity Evaluation of Some Binuclear Metal Complexes of Cu(II) and Zn(II) with Tridentate Schiff Base Ligands
  作者：Akbar Mobinikhaledi、Mojgan Zendehdel、Parvin Safari、Ahmad Hamta、S. Mehdi Shariatzadeh

  DOI：10.1080/15533174.2011.609512

  日期：2012.2.1

  A few kinds of new Schiff bases were synthesized by reaction of 2-aminophenol and corresponding synthesized azo compounds 3a-e. Further reaction of these Schiff bases 4a-e with transition metal salts as Cu(II) and Zn(II) gave corresponding binuclear complexes 5a-e and 6a-e. The antibacterial activity of prepared complexes was investigated against Staphylococcus aureus and Escherichia coli bacteria. The results for some compounds revealed a moderate to good inhibition against Staphylococcus aureus compared with penicillin zone of inhibition.