4-[(1E)-乙烷亚肼基基]苯酚 | 805233-94-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-[(1E)-乙烷亚肼基基]苯酚
• 英文名称: 4-Hydroxy-acetophenon-hydrazon
• 英文别名: p-Hydroxy-acetophenon-hydrazon；1-(4-hydroxy-phenyl)-ethanone-hydrazone；1-(4-Hydroxy-phenyl)-aethanon-hydrazon；4-Ethanehydrazonoylphenol
• CAS: 805233-94-7
• 化学式: C₈H₁₀N₂O
• 分子量: 150.18
• InChiKey: YJGQJJIPPGVQCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(1E)-乙烷亚肼基基]苯酚 在 硫酸 、 sodium nitrite 作用下， 生成 对乙酰氨基酚
  参考文献：
  名称：

  The Rearrangement of Hydrazones and Semicarbazones

  摘要：

  DOI：

  10.1021/ja01119a037
• 作为产物：
  描述：

  2-氯-4'-羟基苯乙酮 在 水 、 一水合肼 、 丙酮 、 sodium iodide 作用下， 反应 2.0h， 生成 4-[(1E)-乙烷亚肼基基]苯酚
  参考文献：
  名称：

  The Reaction of Hydrazine with Some α-Dimethylaminoacetophenones

  摘要：

  DOI：

  10.1021/ja01123a013

文献信息

• Reductive Deoximation of Aryloximes into Hydrocarbons by Hydrazine/KOH: A Novel Application of the Wolff–Kishner Reduction
  作者：H. M. Nanjundaswamy、M. A. Pasha

  DOI：10.1080/00397910600638747

  日期：2006.6

  Abstract We report the reductive deoximation of different substituted aryl, diaryl, and aralkyloximes into the respective methyl or methylene derivatives by hydrazine hydrate/KOH at reflux in satisfactory yields.

  摘要 我们报道了不同的​​取代芳基、二芳基和芳烷基肟通过水合肼/KOH 在回流下以令人满意的产率还原脱肟成各自的甲基或亚甲基衍生物。
• Synthesis of Simple Hydrazones of Carbonyl Compounds by an Exchange Reaction
  作者：G. R. Newkome、D. L. Fishel

  DOI：10.1021/jo01341a008

  日期：1966.3
• Lock; Stach, Chemische Berichte, 1944, vol. 77, p. 293,296
  作者：Lock、Stach

  DOI：——

  日期：——
• Novel 9-(2-(1-arylethylidene)hydrazinyl)acridine derivatives: Target Topoisomerase 1 and growth inhibition of HeLa cancer cells
  作者：Md Rafi Haider、Kamal Ahmad、Nadeem Siddiqui、Zulphikar Ali、Md Jawaid Akhtar、Neeraj Fuloria、Shivkanya Fuloria、Manickam Ravichandran、M. Shahar Yar

  DOI：10.1016/j.bioorg.2019.102962

  日期：2019.7

  A series of 9-(2-(1-arylethylidene)hydrazinyl)acridine and its analogs were designed, synthesized and evaluated for biological activities. Various biochemical assays were performed to determine the free radical scavenging capacity of synthesized compounds (4a-4j). Anticancer activity of these compounds was assessed against two different human cancer cell lines viz cervical cancer cells (HeLa) and liver cancer cells (HepG2) as well as normal human embryonic kidney cell line (HEK 293). Compounds 4b, 4d and 4e showed potential anti-proliferative effects on HeLa cells. Based on results obtained from antioxidant and cytotoxicity studies, 4b, 4d and 4e were further studied in detail for different biological activities. 4b, 4d and 4e reduced the cell growth, inhibited metastatic activity and declined the potential of cell migration in HeLa cell lines. Topoisomerase1 (Top1) treated with compounds 4b, 4d and 4e exhibited inhibition of Top1 and prevented DNA replication. Molecular docking results validate that interaction of compounds 4b, 4d and 4e with Top1-DNA complex, which might be accountable for their inhibitory effects. Further it was concluded that compounds 4b, 4d and 4e arrests the cells at S phase and consequently induces cell death through DNA damage in HeLa cells.