N-(4-硝基-2-((三氟甲基)磺酰基)苯基)乙酰胺 | 54941-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N-(4-硝基-2-((三氟甲基)磺酰基)苯基)乙酰胺
• 英文名称: N-(4-nitro-2-((trifluoromethyl)sulfonyl)phenyl)acetamide
• 英文别名: 2-hydroxy-3-(phenylamino)naphthalene-1,4-dione；2-hydroxy-3-(phenylamino)-1,4-naphthoquinone；2-anilino-3-hydroxy-[1,4]naphthoquinone；2-Anilino-3-hydroxy-[1,4]naphthochinon；2-Hydroxy-3-anilino-1,4-naphthochinon
• CAS: 54941-03-6
• 化学式: C₁₆H₁₁NO₃
• 分子量: 265.268
• InChiKey: BFDCIZJVEBXKKA-UHFFFAOYSA-N

物化性质

• 熔点：
  212 °C
• 沸点：
  425.9±45.0 °C(Predicted)
• 密度：
  1.469±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(4-硝基-2-((三氟甲基)磺酰基)苯基)乙酰胺 、 溴 、 溶剂黄146 生成 2,3-二羟基-1,4-萘醌 、 2,3,4-tribromoaniline
  参考文献：
  名称：

  Zincke; Wiegand, Justus Liebigs Annalen der Chemie, 1895, vol. 286, p. 82

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(N-acetyl-anilino)-3-anilino-[1,4]naphthoquinone 在 氢氧化钾 、 sodium hydroxide 、 溶剂黄146 、 sodium nitrite 作用下， 生成 N-(4-硝基-2-((三氟甲基)磺酰基)苯基)乙酰胺
  参考文献：
  名称：

  Fries; Billig, Chemische Berichte, 1925, vol. 58, p. 1133

  摘要：

  DOI：

文献信息

• Effect of substituents and chain length in amino-1,4-naphthoquinones on glutathione-S-transferase inhibition: molecular docking and electrochemical perspectives: a structure–activity study
  作者：Judith Faúndes、Michelle Muñoz-Osses、Pilar Morales、Federico Tasca、César Zúñiga Loyola、Mario Faúndez、Carolina Mascayano、Juana A. Ibacache

  DOI：10.1039/d2nj04079d

  日期：——

  used. The reactions of the compounds were accomplished in the presence or the absence of Lewis acid as a catalyst. The new derivatives were evaluated as potential inhibitors of the enzyme glutathione-S-transferase (GST) by conjugating reduced glutathione (GSH) with the substrate 1-chloro-2,4-dinitrobenzene (CDNB). The study of the GST activity showed a clear structure–activity relationship in which the

  在这项研究中，合成了基于药效团氨基-1,4-萘醌的新型同源二聚体和单胺化产物。为了进行结构-活性研究，三种前体醌（2,3-二氯-1,4-萘醌、1,4-萘醌和 2-羟基-1,4-萘醌）和四种二胺（4,4'-使用二氨基二苯甲烷、4,4'-乙二苯胺、乙二胺和 1,3-二氨基丙烷）。化合物的反应在路易斯酸作为催化剂存在或不存在的情况下完成。通过将还原型谷胱甘肽 (GSH) 与底物 1-氯-2,4-二硝基苯 (CDNB) 结合，新衍生物被评估为谷胱甘肽-S-转移酶 (GST) 的潜在抑制剂。GST 活性的研究表明，氯化化合物8具有明确的构效关系。是最好的抑制剂，抑制百分比值为57%，与其他GST抑制剂如六氯酚和依他利酸一样在抑制范围内。这些实验结果与分子对接研究一致，分子对接研究表明化合物8与靠近催化位点（G 位点）的酶结合，氯基团显示出对配体的稳定性至关重要。此外，从计算机探索中，注意到亲脂性和酶
• 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.
• Zincke, Chemische Berichte, 1892, vol. 25, p. 3606
  作者：Zincke

  DOI：——

  日期：——
• Discovery of Novel 2-Aniline-1,4-naphthoquinones as Potential New Drug Treatment for Leber’s Hereditary Optic Neuropathy (LHON)
  作者：Carmine Varricchio、Kathy Beirne、Pascale Aeschlimann、Charles Heard、Malgorzata Rozanowska、Marcela Votruba、Andrea Brancale

  DOI：10.1021/acs.jmedchem.0c00942

  日期：2020.11.25

  Leber's hereditary optic neuropathy (LHON) is a rare genetic mitochondrial disease and the primary cause of chronic visual impairment for at least 1 in 10 000 individuals in the U.K. Treatment options remain limited, with only a few drug candidates and therapeutic approaches, either approved or in development. Recently, idebenone has been investigated as drug therapy in the treatment of LHON, although evidence for the efficacy of idebenone is limited in the literature. NAD(P)H:quinone oxidoreductase 1 (NQO1) and mitochondrial complex III were identified as the major enzymes involved in idebenone activity. Based on this mode of action, computer-aided techniques and structure-activity relationship (SAR) optimization studies led to the discovery of a series naphthoquinone-related small molecules, with comparable adenosine 5'-triphosphate (ATP) rescue activity to idebenone. Among these, three compounds showed activity in the nanomolar range and one, 2-((4-fluoro-3-(trifluoromethyl)phenyl)amino)-3-(methylthio)naphthalene-1,3-dione (1), demonstrated significantly higher potency ex vivo, and significantly lower cytotoxicity, than idebenone.