8-hydroxy-2-(piperidin-1-yl)naphthalene-1,4-dione | 64675-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-hydroxy-2-(piperidin-1-yl)naphthalene-1,4-dione
• 英文别名: 8-hydroxy-2-piperidin-1-ylnaphthalene-1,4-dione
• CAS: 64675-49-6
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: LWQGWAOVGLRMRP-UHFFFAOYSA-N

物化性质

• 熔点：
  158 °C
• 沸点：
  458.3±45.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.61
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  8-hydroxy-2-(piperidin-1-yl)naphthalene-1,4-dione 、 硫酸 生成 4,8-dihydroxynaphthalene-1,2-dione
  参考文献：
  名称：

  CAMERON D. W.; SAMUEL E. L., AUSTRAL. J. CHEM. , 1977, 30, NO 9, 2081-2085

  摘要：

  DOI：
• 作为产物：
  描述：

  哌啶 、 3-Bromojuglone 以 溶剂黄146 为溶剂， 以39%的产率得到8-hydroxy-2-(piperidin-1-yl)naphthalene-1,4-dione
  参考文献：
  名称：

  New naphthoquinone derivatives against glioma cells

  摘要：

  This work was aimed to the development of a set of new naphtoquinone derivatives that can act against glioma. The compounds were tested in order to find out their ability to inhibit the growth of glioma cells, and the results of these assays were correlated with electrochemical analysis and NMR-based reoxidation kinetic studies, suggesting that a redox mechanism underlies and may explain the observed biological behavior. In addition to a full description of the synthetic pathways, electrochemistry, NMR and single crystal X-ray diffraction data are provided. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.039

文献信息

• Synthesis of quinone-based heterocycles of broad-spectrum anticancer activity
  作者：Ashraf A Aly、Alaa A Hassan、Nasr K Mohamed、Mohamed Ramadan、Amal S Abd El-Aal、Stefan Bräse、Martin Nieger

  DOI：10.1177/1747519820959737

  日期：2021.5

  A synthesis of benzo[e][1,2,4]triazines and 1,2,4-triazolospiro[4,5]deca-2,6,9-trien-8-ones has been developed from reactions of amidrazones with 2-chloro-1,4-benzoquinone in EtOAc containing 0.5 mL of piperidine. This highly regioselective and one-pot process provided rapid access to 1,2,4-triazolospiro[4,5]deca-2,6,9-trien-8-ones (60%–70%) and benzo[e][1,2,4]triazines (11%–18%). On reacting amidrazones

  苯并[ e ] [1,2,4]三嗪和1,2,4-三唑并螺[4,5] deca-2,6,9-trien-8-ones的合成是由酰胺化with与2含0.5 mL哌啶的EtOAc中的-氯-1,4-苯醌。这种高度区域选择性和一锅法工艺可快速获得1,2,4-三唑并螺[4,5] deca-2,6,9-trien-8-ones（60％–70％）和苯并[ e]] [1,2,4]三嗪（11％–18％）。在酰胺/ with与5-羟基-1，4-萘醌在EtOAc /哌啶混合物中反应后，反应进行，得到5-羟基-2-（哌啶-1-基）萘-1，4-二酮。除X射线结构分析外，还通过红外，NMR（2D-NMR），质谱和元素分析证明了分离产物的结构。讨论了反应机理。所选化合物的抗癌筛选显示了针对大多数黑色素瘤癌细胞系，卵巢癌OVCAR-3，中枢神经系统癌SF-295和U251，非小细胞肺癌NCI-H23，肾癌SN12C和结肠癌