1-(1-(2-methoxyphenyl)ethylidene)hydrazine | 5758-17-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(1-(2-methoxyphenyl)ethylidene)hydrazine
• 英文别名: 2-Methoxy-acetophenon-hydrazon；1-(2-Methoxyphenyl)ethylidenehydrazine
• CAS: 5758-17-8
• 化学式: C₉H₁₂N₂O
• 分子量: 164.207
• InChiKey: RRDOKGKCBDEXIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-氯吖啶 、 1-(1-(2-methoxyphenyl)ethylidene)hydrazine 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以78%的产率得到9-(2-(1-(2-methoxyphenyl)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'-甲氧基苯乙酮 在 三氟化硼乙醚 、 肼 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以84%的产率得到1-(1-(2-methoxyphenyl)ethylidene)hydrazine
  参考文献：
  名称：

  Lewis酸通过肼与苯乙酮和靛红衍生物的反应促进N-未取代的direct的直接合成

  摘要：

  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。

  DOI：

  10.1134/s1070363216120471

文献信息

• Rhodium-Catalyzed Synthesis of Isoquinolines and Indenes from Benzylidenehydrazones and Internal Alkynes
  作者：Xiao-Cheng Huang、Xu-Heng Yang、Ren-Jie Song、Jin-Heng Li

  DOI：10.1021/jo402497v

  日期：2014.2.7

  presented for the selective assembly of isoquinolines and indenes by rhodium-catalyzed tandem cyclization of benzylidenehydrazones with internal alkynes. This method involves the selective cleavage of the N–N bond and the C═N bonds and is dependent on the substituents of the benzylidenehydrazone.

  提出了一种新的路线，用于通过铑催化的亚苄基hydr与内部炔烃的串联催化选择性地组装异喹啉和茚满。该方法涉及N-N键和C═N键的选择性裂解，并且取决于亚苄基hydr的取代基。
• 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
• Unexpected Products of the Reaction of Cyanoacetylhydrazones of Aryl/heteryl Ketones with Hydrazine: A New Route to Aryl/Heteryl Hydrazones, X-ray Structure, and In vitro Anti-proliferative Activity Against NCI 60-cell Line Panel
  作者：Reham A. Mohamed-Ezzat、Benson M. Kariuki、Galal H. Elgemeie

  DOI：10.21608/ejchem.2023.197330.7682

  日期：2023.4.26