tert-butyl 2-((3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)oxy)acetate | 1402666-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl 2-((3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)oxy)acetate
• 英文别名: Tert-butyl 2-(3-methyl-1,4-dioxonaphthalen-2-yl)oxyacetate；tert-butyl 2-(3-methyl-1,4-dioxonaphthalen-2-yl)oxyacetate
• CAS: 1402666-16-3
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: RQAGHFBLNKBOOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-((3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)oxy)acetate 在 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 异丙醇 、 甲苯 为溶剂， 反应 0.25h， 生成 3-(propyl 2-(1,4-dihydro-2-methyl-1,4-dioxonaphthalen-3-yloxy)acetate)triphenylphosphonium bromide
  参考文献：
  名称：

  1,4-Naphthoquinone Cations as Antiplasmodial Agents: Hydroxy-, Acyloxy-, and Alkoxy-Substituted Analogues

  摘要：

  Cations of hydroxy-substituted 1,4-naphthoquinones were synthesized and evaluated as antiplasmodial agents against Plasmodium falciparum. The atovaquone analogues were found to be inactive as antagonists of parasite growth, which was attributed to ionization of the acidic hydroxyl moiety. Upon modification to an alkoxy substituent, the antiplasmodial activity was restored in the sub-100 nM range. Optimal inhibitors were found to possess IC50 values of 17.4 49.5 nM against heteroresistant P. falciparum W2.

  DOI：

  10.1021/ml300242v
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 2-羟基-3-甲基-1,4-萘醌 在 四丁基氟化铵 、 potassium carbonate 、 18-冠醚-6 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以62%的产率得到tert-butyl 2-((3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)oxy)acetate
  参考文献：
  名称：

  1,4-Naphthoquinone Cations as Antiplasmodial Agents: Hydroxy-, Acyloxy-, and Alkoxy-Substituted Analogues

  摘要：

  Cations of hydroxy-substituted 1,4-naphthoquinones were synthesized and evaluated as antiplasmodial agents against Plasmodium falciparum. The atovaquone analogues were found to be inactive as antagonists of parasite growth, which was attributed to ionization of the acidic hydroxyl moiety. Upon modification to an alkoxy substituent, the antiplasmodial activity was restored in the sub-100 nM range. Optimal inhibitors were found to possess IC50 values of 17.4 49.5 nM against heteroresistant P. falciparum W2.

  DOI：

  10.1021/ml300242v

文献信息

• 1,4-Naphthoquinone Cations as Antiplasmodial Agents: Hydroxy-, Acyloxy-, and Alkoxy-Substituted Analogues
  作者：Xiao Lu、Ali Altharawi、Jiri Gut、Philip J. Rosenthal、Timothy E. Long

  DOI：10.1021/ml300242v

  日期：2012.12.13

  Cations of hydroxy-substituted 1,4-naphthoquinones were synthesized and evaluated as antiplasmodial agents against Plasmodium falciparum. The atovaquone analogues were found to be inactive as antagonists of parasite growth, which was attributed to ionization of the acidic hydroxyl moiety. Upon modification to an alkoxy substituent, the antiplasmodial activity was restored in the sub-100 nM range. Optimal inhibitors were found to possess IC50 values of 17.4 49.5 nM against heteroresistant P. falciparum W2.