2-(2,4-dihydroxyphenyl)-8-hydroxynaphthalene-1,4-dione | 1289603-90-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2,4-dihydroxyphenyl)-8-hydroxynaphthalene-1,4-dione
• 英文别名: 2-(2,4-Dihydroxyphenyl)-8-hydroxynaphthalene-1,4-dione
• CAS: 1289603-90-2
• 化学式: C₁₆H₁₀O₅
• 分子量: 282.252
• InChiKey: LWCAHETWUAFCPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2,4-dihydroxyphenyl)-8-hydroxynaphthalene-1,4-dione 在 sodium dithionite 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 0.25h， 以59%的产率得到3-(2,4-dihydroxyphenyl)naphthalene-1,4,5-triol
  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
• 作为产物：
  描述：

  5-羟基对萘醌 、 间苯二酚 在 硫酸 、 溶剂黄146 作用下， 以60 %的产率得到2-(2,4-dihydroxyphenyl)-8-hydroxynaphthalene-1,4-dione
  参考文献：
  名称：

  用于农药发现的天然产物：萘醌类白花丹和胡桃醌的结构多样性推导和生物活性

  摘要：

  病虫害严重影响农作物产量和品质，且难以防治。天然产物是发现新农药的重要来源。本工作以萘醌类白花红素和胡桃醌为母体结构，设计、合成了一系列衍生物，并对其杀菌活性、抗病毒活性和杀虫活性进行了评价。我们首次发现萘醌类化合物对14种真菌具有广谱抗真菌活性。一些萘醌显示出比嘧霉胺更高的杀真菌活性。化合物 I、I-1e 和 II-1a 作为新型抗真菌先导化合物出现，对花生尾孢属具有优异的杀真菌活性（EC50 值：11.35–17.70 µg/mL）。一些化合物还对烟草花叶病毒 (TMV) 表现出良好到极佳的抗病毒活性。化合物 I-1f 和 II-1f 显示出与利巴韦林相似水平的抗 TMV 活性，可作为新的抗病毒候选物。这些化合物还表现出良好到极好的杀虫活性。化合物 II-1d 和 III-1c 对小菜蛾的杀虫活性与苦参碱、氟虫隆和鱼藤酮相似。目前的研究发现了白花丹苷和胡桃醌作为母体结构，为它们在植物保

  DOI：

  10.3390/molecules28083328

文献信息

• Discovery of 5-Hydroxy-1,4-naphthoquinone (Juglone) Derivatives as Dual Effective Agents Targeting Platelet-Cancer Interplay through Protein Disulfide Isomerase Inhibition
  作者：Yu-Pu Juang、Ju-Ying Tsai、Wan-Lan Gu、Hui-Ching Hsu、Chao-Lung Lin、Chin-Chung Wu、Pi-Hui Liang

  DOI：10.1021/acs.jmedchem.3c02107

  日期：2024.3.14

  In this study, a series of 2- and/or 3-substituted juglone derivatives were designed and synthesized. Among them, 9, 18, 22, 30, and 31 showed stronger inhibition activity against cell surface PDI or recombinant PDI and higher inhibitory effects on U46619- and/or collagen-induced platelet aggregation than juglone. The glycosylated derivatives 18 and 22 showed improved selectivity for inhibiting the

  在本研究中，设计并合成了一系列2-和/或3-取代的胡桃酮衍生物。其中， 9、18、22、30和31比胡桃醌表现出更强的对细胞表面PDI或重组PDI的抑制活性以及对U46619和/或胶原诱导的血小板聚集的更高的抑制作用。糖基化衍生物18和22显示出改善的抑制多发性骨髓瘤RPMI 8226细胞增殖的选择性，并且在72小时细胞活力测试中IC 50值分别达到61和48nM。此外， 18和22能够阻止肿瘤细胞诱导的血小板聚集和血小板增强的肿瘤细胞增殖。分子对接显示氨基酸残基 Gln243、Phe440 和 Leu443 对于化合物-蛋白质相互作用很重要。我们的结果揭示了胡桃醌衍生物作为新型抗血小板和抗癌双重药物的潜力，它们可通过与 PDI 催化活性位点共价结合来中断血小板与癌症的相互作用。
• 8-Hydroxynaphthalene-1,4-dione derivative as novel compound for glioma treatment
  作者：Giuseppe Zagotto、Marco Redaelli、Riccardo Pasquale、Domenico D’Avella、Giorgio Cozza、Luca Denaro、Francesca Pizzato、Carla Mucignat-Caretta

  DOI：10.1016/j.bmcl.2011.02.001

  日期：2011.4

  Malignant gliomas continue to demand the search for improved chemotherapeutic solutions. In this work the results of a preliminary in vitro screening performed on a small library of compounds are disclosed. As a result 2-(2,4-dihydroxyphenyl)-8-hydroxy-1,4-naphthoquinone emerged as a promising therapeutic lead. (C) 2011 Elsevier Ltd. All rights reserved.
• New naphthoquinone derivatives against glioma cells
  作者：Marco Redaelli、Carla Mucignat-Caretta、Abdirisak Ahmed Isse、Armando Gennaro、Raffaele Pezzani、Riccardo Pasquale、Valeria Pavan、Marco Crisma、Giovanni Ribaudo、Giuseppe Zagotto

  DOI：10.1016/j.ejmech.2015.04.039

  日期：2015.5

  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.
• Natural Products for Pesticides Discovery: Structural Diversity Derivation and Biological Activities of Naphthoquinones Plumbagin and Juglone
  作者：Kaihua Wang、Beibei Wang、Henan Ma、Ziwen Wang、Yuxiu Liu、Qingmin Wang

  DOI：10.3390/molecules28083328

  日期：——

  seriously affect the yield and quality of crops and are difficult to control. Natural products are an important source for the discovery of new pesticides. In this work, naphthoquinones plumbagin and juglone were selected as parent structures, and a series of their derivatives were designed, synthesized and evaluated for their fungicidal activities, antiviral activities and insecticidal activities. We

  病虫害严重影响农作物产量和品质，且难以防治。天然产物是发现新农药的重要来源。本工作以萘醌类白花红素和胡桃醌为母体结构，设计、合成了一系列衍生物，并对其杀菌活性、抗病毒活性和杀虫活性进行了评价。我们首次发现萘醌类化合物对14种真菌具有广谱抗真菌活性。一些萘醌显示出比嘧霉胺更高的杀真菌活性。化合物 I、I-1e 和 II-1a 作为新型抗真菌先导化合物出现，对花生尾孢属具有优异的杀真菌活性（EC50 值：11.35–17.70 µg/mL）。一些化合物还对烟草花叶病毒 (TMV) 表现出良好到极佳的抗病毒活性。化合物 I-1f 和 II-1f 显示出与利巴韦林相似水平的抗 TMV 活性，可作为新的抗病毒候选物。这些化合物还表现出良好到极好的杀虫活性。化合物 II-1d 和 III-1c 对小菜蛾的杀虫活性与苦参碱、氟虫隆和鱼藤酮相似。目前的研究发现了白花丹苷和胡桃醌作为母体结构，为它们在植物保