2-{[1-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)-1H-1,2,3-triazol-4-yl]methyl}-1H-isoindole-1,3(2H)-dione | 1353244-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-{[1-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)-1H-1,2,3-triazol-4-yl]methyl}-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-[[1-(1,4-Dioxonaphthalen-2-yl)triazol-4-yl]methyl]isoindole-1,3-dione；2-[[1-(1,4-dioxonaphthalen-2-yl)triazol-4-yl]methyl]isoindole-1,3-dione
• CAS: 1353244-64-0
• 化学式: C₂₁H₁₂N₄O₄
• 分子量: 384.351
• InChiKey: UAJQWCLINHYYJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-溴-1,4-萘醌 在 copper(l) iodide 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 2-{[1-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)-1H-1,2,3-triazol-4-yl]methyl}-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Potent naphthoquinones against antimony-sensitive and -resistant Leishmania parasites: Synthesis of novel α- and nor-α-lapachone-based 1,2,3-triazoles by copper-catalyzed azide–alkyne cycloaddition

  摘要：

  Continuing our screening program for novel anti-parasite compounds, we synthesized seven 1,4-naphthoquinones coupled to 1,2,3-triazoles, five nor-beta-lapachone-based 1,2,3-triazoles and ten alpha-lapachone-based 1,2,3-triazoles. These and other naphthoquinonoid compounds were evaluated for their activity against promastigote forms of antimony-sensitive and -resistant strains of Leishmania infantum (syn. Leishmania chagasi) and Leishmania amazonensis. The toxicity of these compounds to mammalian cells was also examined. The substances were more potent than an antimonial drug, with IC50 values ranging from 1.0 to 50.7 mu M. Nor-alpha-lapachone derivatives showed the highest antileishmanial activity, with selectivity indices in the range of 10-15. These compounds emerged as important leads for further investigation as antileishmanial agents. Additionally, one of these compounds exhibited cross-resistance in Sb-resistant Leishmania and could provide a molecular tool for investigating the multidrug resistance mechanisms in Leishmania parasites. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.038

文献信息

• Synthesis of 2-(1H-1,2,3-Triazol-1-yl)-1,4-naphthoquinones from 2-Azido-1,4-naphthoquinone and Terminal Alkynes
  作者：Ronaldo de Oliveira、Wilson do Nascimento、Celso Camara

  DOI：10.1055/s-0030-1260172

  日期：2011.10

  A series of 2-[(4-substituted 1H-1,2,3-triazol-1-yl)-1,4-naphthoquinones were prepared in moderate-to-good yields (51-90%) by the reaction of 2-azido-1,4-naphthoquinone with terminal alkynes in the presence of a catalytic amounts of copper(I) iodide in acetonitrile. quinones - triazoles - heterocycles - copper catalysis - cycloaddition­ - alkynes - click chemistry

  通过中和高产率（51-90％）制备一系列2-[（4-取代的1 H -1,2,3-三唑-1-基）-1,4-萘醌。在催化量的碘化铜（I）在乙腈中的存在下，将2-叠氮基-1,4-萘醌与末端炔烃联用。 醌-三唑-杂环-铜催化-环加成反应-炔烃-点击化学