2-Chlor-acetophenon-hydrazon | 5758-16-7

• 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: 2-Chlor-acetophenon-hydrazon
• 英文别名: 1-(2-Chlorophenyl)ethylidenehydrazine
• CAS: 5758-16-7
• 化学式: C₈H₉ClN₂
• 分子量: 168.626
• InChiKey: YQPJGZUBIXMDGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  38.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-氯吖啶 、 2-Chlor-acetophenon-hydrazon 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以77%的产率得到9-(2-(1-(2-chlorophenyl)ethylidene)hydrazinyl)acridine
  参考文献：
  名称：

  Novel 9-(2-(1-arylethylidene)hydrazinyl)acridine derivatives: Target Topoisomerase 1 and growth inhibition of HeLa cancer cells

  摘要：

  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.

  DOI：

  10.1016/j.bioorg.2019.102962
• 作为产物：
  描述：

  2-Chlor-acetophenon- 在 肼 作用下， 以 乙醇 为溶剂， 生成 2-Chlor-acetophenon-hydrazon
  参考文献：
  名称：

  Synthesis of Simple Hydrazones of Carbonyl Compounds by an Exchange Reaction

  摘要：

  DOI：

  10.1021/jo01341a008

文献信息

• Eosin‐Y‐Catalyzed Photoredox C−S Bond Formation: Easy Access to Thioethers
  作者：Shiv Chand、Anand Kumar Pandey、Rahul Singh、Saurabh Kumar、Krishna Nand Singh

  DOI：10.1002/asia.201901060

  日期：2019.12.13

  An operationally simple Eosin Y catalyzed sulfenylation of hydrazones has been realized to afford a range of thioethers under visible light. The methodology provides high yields of thioethers under ambient conditions employing readily available and inexpensive starting materials. The reaction has broad substrate scope and is compatible with various functional groups.

  已经实现了操作上简单的曙红Y催化的亚磺酰基化，以在可见光下提供一系列硫醚。该方法使用容易获得和廉价的起始原料在环境条件下提供了高产率的硫醚。该反应具有广泛的底物范围并且与各种官能团相容。
• Lewis acid-promoted direct synthesis of N-unsubstituted hydrazones via the reaction of hydrazine with acetophenone and isatin derivatives
  作者：A. S. El-Azab、H. A. Ghabbour、W. M. El-Husseiny、A. R. Maarouf、M. A. Mohamed、A. A.-M. Abdel-Aziz

  DOI：10.1134/s1070363216120471

  日期：2016.12

  Hydrazones 2–22 were synthesized via the reaction of acetophenone with isatin derivatives and anhydrous hydrazine promoted by BF3 as a Lewis acid at 0°C. Structures of the synthesized hydrazones were determined on the basis of NMR and X-ray crystallographic analyses.

  0 2–22是通过苯乙酮与靛红衍生物和BF3作为路易斯酸在0°C促进的无水肼反应而合成的。基于NMR和X射线晶体学分析确定合成的hydr的结构。
• Iron-catalyzed intermolecular cycloaddition of diazo surrogates with hexahydro-1,3,5-triazines
  作者：Pei Liu、Chenghao Zhu、Guangyang Xu、Jiangtao Sun

  DOI：10.1039/c7ob02115a

  日期：——

  We report here an unprecedented iron-catalyzed cycloaddition reaction of diazo surrogates with hexahydro-1,3,5-triazines, providing five-membered heterocycles in moderate to high yields under mild reaction conditions. This cycloaddition features C–N and C–C bond formation using a cheap iron catalyst. Importantly, different to our former report on a gold-catalyzed system, both donor/donor and donor/acceptor

  我们在这里报告了前所未有的铁催化重氮代孕酸酯与六氢-1,3,5-三嗪的铁催化环加成反应，在温和的反应条件下以中等至高收率提供了五元杂环。这种环加成反应使用廉价的铁催化剂可形成C–N和C–C键。重要的是，与我们先前关于金催化体系的报告不同，在该铁催化方案中，供体/供体和供体/受体重氮底物都可以耐受。