2-hydroxy-3-[(4-methoxyphenyl)amino]-1,4-napthoquinone | 109090-67-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-3-[(4-methoxyphenyl)amino]-1,4-napthoquinone
• 英文别名: 2-hydroxy-3-((4-methoxyphenyl)amino)naphthalene-1,4-dione；2-hydroxy-3-(4-methoxy-anilino)-[1,4]naphthoquinone；2-Hydroxy-3-(4-methoxy-anilino)-[1,4]naphthochinon；2-Hydroxy-3-<(4'-methoxy-phenyl)-amino>-naphthochinon-(1,4)；2-(4-Methoxy-anilino)-3-hydroxy-naphthochinon-(1,4)
• CAS: 109090-67-7
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: DMYHGSSGVCLQQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1,4-萘醌 在 双氧水 、 sodium carbonate 、 zinc(II) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 4.33h， 生成 2-hydroxy-3-[(4-methoxyphenyl)amino]-1,4-napthoquinone
  参考文献：
  名称：

  Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase

  摘要：

  Schistosomiasis ranks second only to malaria as the most common parasitic disease worldwide. 700 million people are at risk and 240 million are already infected. Praziquantel is the anthelmintic of choice but decreasing efficacy has already been documented. In this work, we exploited the inhibition of Schistosoma mansoni dihydroorotate dehydrogenase (SmDHODH) as a strategy to develop new therapeutics to fight schistosomiasis. A series of quinones (atovaquone derivatives and precursors) was evaluated regarding potency and selectivity against both SmDHODH and human DHODH. The best compound identified is 17 (2-hydroxy-3-isopentylnaphthalene-1,4-dione) with IC50 = 23 +/- 4 nM and selectivity index of 30.83. Some of the new compounds are useful pharmacological tools and represent new lead structures for further optimization. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.02.018

文献信息

• In vivo antimalarial activity of novel 2-hydroxy-3-anilino-1,4-naphthoquinones obtained by epoxide ring-opening reaction
  作者：Lucas Cunha Dias de Rezende、Fernando Fumagalli、Marraiana Schiavon Bortolin、Marianne Garcia de Oliveira、Murilo Helder de Paula、Valter Ferreira de Andrade-Neto、Flavio da Silva Emery

  DOI：10.1016/j.bmcl.2013.06.033

  日期：2013.8

  1,4-Naphthoquinone derivatives are known to have relevant activities against several parasites. Among the treatment options for malaria, atovaquone, a 1,4-naphthoquinone derivative, is widely applied in the treatment and prophylaxis of such disease. Based on the structure simplification of atovaquone, we designed and synthesized four novel naphthoquinoidal derivatives. The compounds were obtained by the underexplored epoxide-opening reaction of 1,4-naphthoquinone using aniline derivatives as nucleophiles. The antiplasmodial activity of the synthesized compounds was performed in vivo using Peter's 4 days suppression test. Significant parasitemia reduction and increased survival were observed for some of the compounds. (C) 2013 Elsevier Ltd. All rights reserved.
• Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase
  作者：Felipe A. Calil、Juliana S. David、Estela R.C. Chiappetta、Fernando Fumagalli、Rodrigo B. Mello、Franco H.A. Leite、Marcelo S. Castilho、Flavio S. Emery、M.Cristina Nonato

  DOI：10.1016/j.ejmech.2019.02.018

  日期：2019.4

  Schistosomiasis ranks second only to malaria as the most common parasitic disease worldwide. 700 million people are at risk and 240 million are already infected. Praziquantel is the anthelmintic of choice but decreasing efficacy has already been documented. In this work, we exploited the inhibition of Schistosoma mansoni dihydroorotate dehydrogenase (SmDHODH) as a strategy to develop new therapeutics to fight schistosomiasis. A series of quinones (atovaquone derivatives and precursors) was evaluated regarding potency and selectivity against both SmDHODH and human DHODH. The best compound identified is 17 (2-hydroxy-3-isopentylnaphthalene-1,4-dione) with IC50 = 23 +/- 4 nM and selectivity index of 30.83. Some of the new compounds are useful pharmacological tools and represent new lead structures for further optimization. (C) 2019 Elsevier Masson SAS. All rights reserved.