2-(2,4-dihydroxyphenyl)naphthalene-1,4-dione | 51595-08-5

• 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)naphthalene-1,4-dione
• 英文别名: 2-(2,4-dihydroxy-phenyl)-[1,4]naphthoquinone；2-(2,4-Dihydroxy-phenyl)-[1,4]naphthochinon；2-(2,4-Dihydroxyphenyl)-1,4-naphthochinon；(2,4-Dihydroxyphenyl)-1,4-naphthochinon
• CAS: 51595-08-5
• 化学式: C₁₆H₁₀O₄
• 分子量: 266.253
• InChiKey: UCXAHZHOALGPIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 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：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,4-dihydroxyphenyl)naphthalene-1,4-dione 在 sodium dithionite 作用下， 生成 2-(2,4-Dihydroxyphenyl)-1,4-naphthochinon
  参考文献：
  名称：

  Hoegberg,H.-E., Acta Chemica Scandinavica (1947), 1973, vol. 27, p. 2559 - 2566

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2,4-Dihydroxyphenyl)-1,4-naphthochinon 在 三氯化铁 、 溶剂黄146 作用下， 生成 2-(2,4-dihydroxyphenyl)naphthalene-1,4-dione
  参考文献：
  名称：

  Pummerer; Huppmann, Chemische Berichte, 1927, vol. 60, p. 1449

  摘要：

  DOI：

文献信息

• The tyrosinase-inhibitory effects of 2-phenyl-1,4-naphthoquinone analogs: importance of the (E)-β-phenyl-α,β-unsaturated carbonyl scaffold of an endomethylene type
  作者：Sultan Ullah、Jinia Akter、Su J. Kim、Jungho Yang、Yujin Park、Pusoon Chun、Hyung R. Moon

  DOI：10.1007/s00044-018-2267-9

  日期：2019.1

  (IC50 = 22.00 ± 1.63 μM), more potently inhibited mushroom tyrosinase than kojic acid (IC50 = 37.86 ± 2.21 μM). Cell-based assays using B16F10 cells (a melanoma cell line) showed 1c dose-dependently suppressed melanin production and more potently inhibited tyrosinase activity than kojic acid. Docking simulation results between 1c and tyrosinase and a kinetic study suggest that 1c is a competitive inhibitor

  为了研究内亚甲基型的（E）-β-苯基-α，β-不饱和羰基支架对酪氨酸酶抑制的影响，通过将取代苯的迈克尔加成到2-苯基-1,4-萘醌衍生物1,4-萘醌，随后发生自氧化。大多数衍生物都有效抑制蘑菇酪氨酸酶，包括1c（IC 50  = 22.00±1.63μM），比曲酸（IC 50  = 37.86±2.21μM）更有效地抑制蘑菇酪氨酸酶。使用B16F10细胞（黑色素瘤细胞系）的基于细胞的分析显示1c与曲酸相比，剂量依赖性地抑制黑色素的产生并更有效地抑制酪氨酸酶的活性。1c和酪氨酸酶之间的对接模拟结果以及动力学研究表明1c是与酪氨酸酶活性位点结合的竞争性抑制剂。这些结果支持萘醌衍生物的抗黑素生成作用是由于其酪氨酸酶抑制活性，并且内亚甲基型的（E）-β-苯基-α，β-不饱和羰基支架可以赋予酪氨酸酶抑制活性。
• One-pot synthesis of indole-fused nitrogen heterocycles <i>via</i> the direct C(sp²)–H functionalization of naphthoquinones; accessibility for deep red emitting materials
  作者：Subramaniyan Prasanna Kumari、Savarimuthu Philip Anthony、Subramaniapillai Selva Ganesan

  DOI：10.1039/d2nj02024f

  日期：——

  A convenient one-pot, two-step methodology was developed for the transformation of readily available planar naphthoquinone derivatives into structurally complex indole-fused nitrogen heterocycles under aerobic conditions.

  一种方便的一锅法、两步法方法被开发出来，用于将易得的平面萘醌衍生物在氧气存在下转化为结构复杂的吲哚-融合氮杂环化合物。
• 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.
• HOEGBERG H. E., J. CHEM. SOC. PERKIN TRANS., 1979, PART 1, NO 10, 2517-2520
  作者：HOEGBERG H. E.

  DOI：——

  日期：——
• Pummerer; Huppmann, Chemische Berichte, 1927, vol. 60, p. 1449
  作者：Pummerer、Huppmann

  DOI：——

  日期：——