2-phenyl-3-(piperidin-1-yl)naphthalene-1,4-dione | 881974-30-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-phenyl-3-(piperidin-1-yl)naphthalene-1,4-dione
• 英文别名: 2-Phenyl-3-piperidin-1-ylnaphthalene-1,4-dione
• CAS: 881974-30-7
• 化学式: C₂₁H₁₉NO₂
• 分子量: 317.387
• InChiKey: NCCCLSLIJSPBTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴-1,4-萘醌 在 palladium diacetate 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-phenyl-3-(piperidin-1-yl)naphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis, reactive oxygen species generation and copper-mediated nuclease activity profiles of 2-aryl-3-amino-1,4-naphthoquinones

  摘要：

  Here we report a series of 2-aryl-3-amino-1,4-naphthoquinones that generated reactive oxygen species (ROS) such as superoxide and hydrogen peroxide upon incubation in pH 7.4 under ambient aerobic conditions. ROS generation from these compounds was sensitive to structural modifications at the 3-amino position and a 2-aryl substituent promoted ROS generation. A number of these compounds were found to induce DNA damage in the presence of Cu(II) without any added reducing agent. Our data suggests that 2-aryl-3-amino-1,4-naphthoquinones' propensity to produce ROS correlated well with its DNA damage inducing ability. 2-Phenyl-3-pyrrolid-1-yl-1,4-naphthoquinone (22) was found to damage DNA at 1 mu M suggesting that these compounds may have therapeutic relevance in targeting cancers which over-express Cu(II) (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.009

文献信息

• BiCl₃ catalyzed synthesis of 2-amino-1,4-naphthoquinones and 1,4-naphthoquinon-2-sulfides and one-pot sequential amine-arylation of 1,4-naphthoquinone
  作者：Mayurakhi Bhuyan、Gakul Baishya

  DOI：10.1039/d2ob01792j

  日期：——

  Using the Lewis acid catalyst BiCl3, a new method for the synthesis of 2-amino-1,4-naphthoquinones and 1,4-naphthoquinon-2-sulfides from 1,4-naphthoquinone has been devised. This method has a broad substrate scope and product extraction is easy. It is low-cost, requires mild and sustainable reaction conditions and results in superior product yields. Additionally, this study presents the first technique

  使用路易斯酸催化剂BiCl 3，设计了一种从1,4-萘醌合成2-氨基-1,4-萘醌和1,4-萘醌-2-硫化物的新方法。该方法底物适用范围广，产物提取容易。它成本低廉，需要温和且可持续的反应条件，并可提高产品收率。此外，本研究提出了第一种用胺和芳基肼/K 2 S 2 O 8进行单锅顺序胺芳基化的技术直接从 1,4-萘醌生产芳基化 2-氨基-1,4-萘醌。这种从经历自由基偶联反应的芳基肼产生芳基自由基的操作上直接的通过自由基捕获控制实验得到了很好的证明。