8-hydroxy-2-(phenylamino)naphthalene-1,4-dione | 109621-29-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-hydroxy-2-(phenylamino)naphthalene-1,4-dione
• 英文别名: 2-Anilino-8-hydroxynaphthalene-1,4-dione；2-anilino-8-hydroxynaphthalene-1,4-dione
• CAS: 109621-29-6
• 化学式: C₁₆H₁₁NO₃
• 分子量: 265.268
• InChiKey: KTEVSOYDEBXIGZ-UHFFFAOYSA-N

物化性质

• 熔点：
  228 °C
• 沸点：
  487.4±45.0 °C(Predicted)
• 密度：
  1.442±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-hydroxy-2-(phenylamino)naphthalene-1,4-dione 在 盐酸 作用下， 生成 4,8-dihydroxynaphthalene-1,2-dione
  参考文献：
  名称：

  juglone系列研究；羟基和羟基卤代衍生物。

  摘要：

  DOI：

  10.1021/jo01164a015
• 作为产物：
  描述：

  1,5-二羟基萘 在 孟加拉红内酯 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 5-hydroxy-2-(phenylamino)naphthalene-1,4-dione 、 8-hydroxy-2-(phenylamino)naphthalene-1,4-dione
  参考文献：
  名称：

  氧化还原循环苯氨基juglones的幽门螺杆菌生长的体外抑制。

  摘要：

  幽门螺杆菌感染会使患胃癌的风险增加10倍。Juglone是一种天然存在的1,4-萘醌，可通过干扰幽门螺杆菌的某些关键代谢途径来阻止幽门螺杆菌的生长。在这里，我们报告设计，合成和体外评估一系列juglone衍生物，即2 / 3-苯基氨基juglones，作为潜在的幽门螺杆菌生长抑制剂。结果表明，5超过了12 phenylaminojuglones（在1.5  μ克/毫升）是1.5-2.2倍胡桃醌更活跃。有趣的是，大多数苯氨基聚醚（12个中的10个）的活性是甲硝唑（一种已知的幽门螺杆菌）的1.1-2.8倍。生长抑制剂。活性最高的化合物2-（（（3,4,5-三甲氧基苯基）氨基）-5-羟基萘-1,4-二酮7]的生长抑制晕环（HGI = 32.25 mm）明显高于juglone和甲硝唑（HGI = 14.50和11.67 mm）。该系列的结构活性关系表明，Juglone支架中氮取代基的性质和位置可能

  DOI：

  10.1155/2018/1618051

文献信息

• Structure-Based Design of a Dual-Targeted Covalent Inhibitor Against Papain-like and Main Proteases of SARS-CoV-2
  作者：Wenying Yu、Yucheng Zhao、Hui Ye、Nanping Wu、Yixian Liao、Nannan Chen、Zhiling Li、Ning Wan、Haiping Hao、Honggao Yan、Yibei Xiao、Maode Lai

  DOI：10.1021/acs.jmedchem.2c00954

  日期：2022.12.22

  maximum rate of the covalent inactivation is comparable to that of the most potent inhibitors reported for the viral proteases and covalent inhibitor drugs currently in clinical use. The covalent inhibition appears to be very specific for the viral proteases. The inhibitor has a potent antiviral activity against SARS-CoV-2 and is also well tolerated by mice and rats in toxicity studies. These results suggest

  SARS-CoV-2 的两种蛋白酶 PL pro和 M pro对于病毒的复制至关重要。使用基于结构的共药效团筛选方法，我们开发了一种新型双靶向抑制剂，该抑制剂对抑制SARS-CoV-2 的PL pro和 M pro具有同等效力。该抑制剂含有一种新型弹头，可以与任一酶的催化半胱氨酸残基形成共价键。共价失活的最大速率与目前临床使用的病毒蛋白酶和共价抑制剂药物报道的最有效的抑制剂相当。共价抑制似乎对病毒蛋白酶非常具有特异性。该抑制剂对 SARS-CoV-2 具有有效的抗病毒活性，并且在毒性研究中也被小鼠和大鼠良好耐受。这些结果表明，该抑制剂是开发治疗 COVID-19 药物的有希望的先导药物。
• Fluorescent 1,4-Naphthoquinones To Visualize Diffuse and Dense-Core Amyloid Plaques in APP/PS1 Transgenic Mouse Brains
  作者：Naewoo Neo Shin、Hanna Jeon、Youngeun Jung、Seungyeop Baek、Sejin Lee、Hee Chan Yoo、Gi Hun Bae、Keunwan Park、Seung-Hoon Yang、Jung Min Han、Ikyon Kim、YoungSoo Kim

  DOI：10.1021/acschemneuro.9b00093

  日期：2019.6.19

  Recent clinical approvals of brain imaging radiotracers targeting amyloid-beta provided clinicians the tools to detect and confirm Alzheimer's disease pathology without autopsy or biopsy. While current imaging agents are effective in postsymptomatic Alzheimer's patients, there is much room for improvement in earlier diagnosis, hence prompting a need for new and improved amyloid imaging agents. Here we synthesized 41 novel 1,4-naphthoquinone derivatives and initially discovered 14 antiamyloidogenic compounds via in vitro amyloid-beta aggregation assay; however, qualitative analyses of these compounds produced conflicting results and required further investigation. Follow-up docking and biophysical studies revealed that four of these compounds penetrate the blood-brain barrier, directly bind to amyloid-beta aggregates, and enhance fluorescence properties upon interaction. These compounds specifically stain both diffuse and dense-core amyloid-beta plaques in brain sections of APP/PS1 double transgenic Alzheimer's mouse models. Our findings suggest 1,4-naphthoquinones as a new scaffold for amyloid-beta imaging agents for early stage Alzheimer's.
• THE CHLORINATION OF 1,5-DIHYDROXYNAPHTHALENE
  作者：R. H. THOMSON

  DOI：10.1021/jo01161a008

  日期：1948.5
• Mylius, Chemische Berichte, 1885, vol. 18, p. 469
  作者：Mylius

  DOI：——

  日期：——
• Anticancer activity and SAR studies of substituted 1,4-naphthoquinones
  作者：Deepak Bhasin、Somsundaram N. Chettiar、Jonathan P. Etter、May Mok、Pui-Kai Li

  DOI：10.1016/j.bmc.2013.05.017

  日期：2013.8

  In this paper, we report the structure-activity relationship studies of substituted 1,4-naphthoquinones for its anticancer properties. 1,4-Naphthoquinone, Juglone, Menadione, Plumbagin and LLL12.1 were used as lead molecules to design PD compounds. Most of the PD compounds showed improved antiproliferative activity in comparison to the lead molecule in prostate (DU-145), breast (MDA-MB-231) and colon (HT-29) cancer cell lines. PD9, PD10, PD11, PD13, PD14 and PD15 were found to be the most potent compound with an IC50 value of 1-3 mu M in all cancer cell lines. Fluorescent polarization assay was employed to study the inhibition of STAT3 dimerization by PD compounds. PD9 and PD18 were found to be potent STAT3 dimerization inhibitors. (C) 2013 Published by Elsevier Ltd.