2-(p-tolylthio)-8-hydroxynaphthalene-1,4-dione | 68963-21-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(p-tolylthio)-8-hydroxynaphthalene-1,4-dione
• 英文别名: 8-Hydroxy-2-(p-tolylsulfanyl)naphthalene-1,4-dione；8-hydroxy-2-(4-methylphenyl)sulfanylnaphthalene-1,4-dione
• CAS: 68963-21-3
• 化学式: C₁₇H₁₂O₃S
• 分子量: 296.346
• InChiKey: UTUVXACKBRZOOY-UHFFFAOYSA-N

物化性质

• 熔点：
  171 °C
• 沸点：
  503.6±50.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(p-tolylthio)-8-hydroxynaphthalene-1,4-dione 在 sodium hydroxide 、 硫酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以90%的产率得到4,8-dihydroxynaphthalene-1,2-dione
  参考文献：
  名称：

  Synthesis of new 9-hydroxy-α- and 7-hydroxy-β-pyran naphthoquinones and cytotoxicity against cancer cell lines

  摘要：

  研究人员开发了一种合成方法，以获得芳香环上具有羟基取代基的δ-和δ-吡喃萘醌10和11。从 8-hydroxy-lawsone 中得到了两个系列的 α- 和 β-pyran 萘醌，并评估了它们对四种肿瘤细胞系的抗癌特性。总的来说，新化合物显示出良好的活性，这可能表明这些化合物具有更强的抗氧化能力。用这种方法成功地制备了天然产物δ-拉帕醌和δ-拉帕醌的9-羟基-δ-拉帕醌和7-羟基-δ-拉帕醌类似物。

  DOI：

  10.1039/c1ob05209h
• 作为产物：
  描述：

  2,3-dichloro-5-hydroxy-2,3-dihydro-[1,4]naphthoquinone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.75h， 生成 2-(p-tolylthio)-8-hydroxynaphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis, molecular docking, and biological activity of thioether derived from juglone in preclinical models of chronic myeloid leukemia

  摘要：

  DOI：

  10.1016/j.comtox.2021.100197

文献信息

• Asymmetric Synthesis of Rubiginones A2 and C2 and Their 11-Methoxy Regioisomers
  作者：M. Carmen Carreño、Álvaro Somoza、María Ribagorda、Antonio Urbano

  DOI：10.1002/chem.200600809

  日期：2007.1.12

  sulfoxide elimination. An efficient opposite regioselection in the cycloaddition step was achieved in the convergent construction of the tetracyclic skeleton using a sulfoxide at C-2 or C-3 of the dienophiles 5 or 6, derived from 5-methoxy-1,4-naphthoquinone. The second domino process, triggered by oxygen and sunlight, allowed the transformation of the initial tetracyclic adducts into the final products

  安古环素类天然产物茜草酮A（2）（2）和C（2）（1）及其11-甲氧基区域异构体3a和3b的融合对映选择性合成是通过使用两个对映体纯的1的多米诺过程实现的-乙烯基环己烯4.合成该二烯的关键步骤是在（SS）-[[（对甲苯基亚磺酰基）甲基]-对-喹诺酚（9）上立体选择性共轭加成AlMe（3）和消除β-羟基亚砜片段，氧化成砜后，回收羰基。第一多米诺序列包括与亚磺酰基萘醌的Diels-Alder反应，然后消除亚砜。在四烯骨架的收敛构造中，使用二烯亲二物5或6的C-2或C-3处的亚砜，在环加成步骤中实现了有效的相对区域选择。衍生自5-甲氧基-1,4-萘醌。第二个多米诺骨牌工艺是由氧气和阳光触发的，它使最初的四环加合物在B环芳构化，甲硅烷基脱保护和C-1氧化后转化为最终产物。
• 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。
• 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.
• Synthesis and antifungal activity of 2/3-arylthio- and 2,3-bis(arylthio)-5-hydroxy-/5-methoxy-1,4-naphthoquinones
  作者：Chung-Kyu Ryu、Ju-Yeon Shim、Mi Jin Chae、Ik Hwa Choi、Ja-Young Han、Ok-Jai Jung、Jung Yoon Lee、Seong Hee Jeong

  DOI：10.1016/j.ejmech.2004.12.004

  日期：2005.5

  2/3-Arylthio- and 2,3-bis(arylthio)-5-hydroxy-/5-methoxy-1,4-naphthoquinones 5-9 were synthesized and tested for in vitro antifungal activity against Candida species and Aspergillus niger. The synthesized compounds 5-9 generally showed good activities against Candida albicans and C tropicalis. The results suggest that the 1,4-naphthoquinones 5-9 would be potent antifungal agents. (c) 2005 Elsevier SAS. All rights reserved.
• Studies in the Juglone Series. III. Addition Reactions
  作者：R. H. Thomson

  DOI：10.1021/jo50001a010

  日期：1951.7