5-hydroxy-2-(4-tolylthio)naphthalene-1,4-dione | 116595-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-hydroxy-2-(4-tolylthio)naphthalene-1,4-dione
• 英文别名: 5-hydroxy-2-(p-tolylthio)naphthalene-1,4-dione；5-hydroxy-2-p-tolylsulfanyl-[1,4]naphthoquinone；5-Hydroxy-2-p-tolylmercapto-[1,4]naphthochinon；5-hydroxy-2-(4-methylphenyl)sulfanylnaphthalene-1,4-dione
• CAS: 116595-17-6
• 化学式: C₁₇H₁₂O₃S
• 分子量: 296.346
• InChiKey: KBVXTFZUCAKBAU-UHFFFAOYSA-N

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

• 作为产物：
  描述：

  5-羟基对萘醌 在 四(三苯基膦)钯 、 溴 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 10.23h， 生成 5-hydroxy-2-(4-tolylthio)naphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis and antifungal activity of 2/3-arylthio- and 2,3-bis(arylthio)-5-hydroxy-/5-methoxy-1,4-naphthoquinones

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2004.12.004

文献信息

• Synthesis of new 9-hydroxy-α- and 7-hydroxy-β-pyran naphthoquinones and cytotoxicity against cancer cell lines
  作者：David R. da Rocha、Ana C. G. de Souza、Jackson A. L. C. Resende、Wilson C. Santos、Evelyne A. dos Santos、Cláudia Pessoa、Manoel O. de Moraes、Letícia V. Costa-Lotufo、Raquel C. Montenegro、Vitor F. Ferreira

  DOI：10.1039/c1ob05209h

  日期：——

  A synthetic method to obtain α- and β-pyran naphthoquinones 10 and 11 with a hydroxyl substituent on the aromatic ring was developed. Two series of α- and β-pyran naphthoquinones were obtained from the 8-hydroxy-lawsone, and their anticancer properties were evaluated against four tumor cell lines. In general, the new compounds displayed good activity, possibly indicating that these compounds have increased pro-oxidant capacity. The 9-hydroxy-α-lapachone and 7-hydroxy-β-lapachone analogues of the natural products α-lapachone and β-lapachone were successfully produced by this methodology.

  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。
• Synthesis, molecular docking, and biological activity of thioether derived from juglone in preclinical models of chronic myeloid leukemia
  作者：Adrhyann J. de S. Portilho、Carinne B. S. M. R. Gomes、Caroline S. Moreira、Luana da S. M. Forezi、Pâmella S. Cordeiro、Vanessa do Nascimento、Julio P. Daniel、Marne C. Vasconcellos、Maria E. A. de Moraes、Caroline de F. A. Moreira-Nunes、Vitor F. Ferreira、Raquel C. Montenegro、David R. da Rocha

  DOI：10.1016/j.comtox.2021.100197

  日期：2021.11
• Studies in the Juglone Series. III. Addition Reactions
  作者：R. H. Thomson

  DOI：10.1021/jo50001a010

  日期：1951.7
• 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.