N-(4-((8-methoxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)oxy)phenyl)acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(4-((8-methoxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)oxy)phenyl)acetamide
• 英文别名: N-[4-(8-methoxy-1,4-dioxonaphthalen-2-yl)oxyphenyl]acetamide
• 化学式: C₁₉H₁₅NO₅
• 分子量: 337.332
• InChiKey: BVVJGNZBFKMBCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对乙酰氨基酚 、 2-溴-8-甲氧基萘-1,4-二酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以57%的产率得到N-(4-((8-methoxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)oxy)phenyl)acetamide
  参考文献：
  名称：

  2-Phenoxy-1,4-naphthoquinones: From a Multitarget Antitrypanosomal to a Potential Antitumor Profile

  摘要：

  A small library of 2-phenoxy-1,4-naphthoquinone and 2-phenoxy-1,4-anthraquinone derivatives was initially developed to optimize the antitrypanosomatid profile of the multitarget hit compound B6 (1). The whole series was evaluated against the three most important human trypanosomatid pathogens (Trypanosoma brucei rhodesiense, Trypanosoma cruzi, and Leishmania donovani), and two compounds (14 and 21) showed good activity, despite a concomitant mammalian cytotoxicity. Furthermore, a subset also inhibited the glycolytic TbGAPDH enzyme in vitro. In light of these results and aware of the antitumor properties of quinones, the anticancer potential of some selected derivatives was investigated. Intriguingly, the tested compounds displayed antitumor activity, while being less toxic against noncancerous cells. The observed cytotoxic potency was ascribed to a multitarget mechanism of action accounting for hGAPDH inhibition and mitochondrial toxicity. Overall, the development of further derivatives, able to finely modulate multiple pathways of cancer or parasite cell metabolism, might lead to more effective treatments against these devastating diseases.

  DOI：

  10.1021/acs.jmedchem.5b00748

文献信息

• 2-Phenoxy-1,4-naphthoquinones: From a Multitarget Antitrypanosomal to a Potential Antitumor Profile
  作者：Federica Prati、Christian Bergamini、Maria Teresa Molina、Federico Falchi、Andrea Cavalli、Marcel Kaiser、Reto Brun、Romana Fato、Maria Laura Bolognesi

  DOI：10.1021/acs.jmedchem.5b00748

  日期：2015.8.27

  A small library of 2-phenoxy-1,4-naphthoquinone and 2-phenoxy-1,4-anthraquinone derivatives was initially developed to optimize the antitrypanosomatid profile of the multitarget hit compound B6 (1). The whole series was evaluated against the three most important human trypanosomatid pathogens (Trypanosoma brucei rhodesiense, Trypanosoma cruzi, and Leishmania donovani), and two compounds (14 and 21) showed good activity, despite a concomitant mammalian cytotoxicity. Furthermore, a subset also inhibited the glycolytic TbGAPDH enzyme in vitro. In light of these results and aware of the antitumor properties of quinones, the anticancer potential of some selected derivatives was investigated. Intriguingly, the tested compounds displayed antitumor activity, while being less toxic against noncancerous cells. The observed cytotoxic potency was ascribed to a multitarget mechanism of action accounting for hGAPDH inhibition and mitochondrial toxicity. Overall, the development of further derivatives, able to finely modulate multiple pathways of cancer or parasite cell metabolism, might lead to more effective treatments against these devastating diseases.