ethyl 1-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)-1H-1,2,3-triazole-4-carboxylate | 1353244-61-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 1-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)-1H-1,2,3-triazole-4-carboxylate
• 英文别名: Ethyl 1-(1,4-dioxonaphthalen-2-yl)triazole-4-carboxylate
• CAS: 1353244-61-7
• 化学式: C₁₅H₁₁N₃O₄
• 分子量: 297.27
• InChiKey: GMJCQWVIXYTWNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  91.2
• 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， 反应 20.0h， 生成 ethyl 1-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)-1H-1,2,3-triazole-4-carboxylate
  参考文献：
  名称：

  On the search for potential anti-Trypanosoma cruzi drugs: Synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions

  摘要：

  Five 2-hydroxy-3-substituted-aminomethyl naphthoquinones, nine 1,2,3-triazolic para-naphthoquinones, five nor-beta-lapachone-based 1,2,3-triazoles, and several other naphthoquinonoid compounds were synthesized and evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological agent of Chagas disease, continuing our screening program for new trypanocidal compounds. Among all the substances, 16-18, 23, 25-29 and 30-33 were herein described for the first time and fifteen substances were identified as more potent than the standard drug benznidazole, with IC50/24 h values in the range of 10.9-101.5 mu M. Compounds 14 and 19 with Selectivity Index of 18.9 and 6.1 are important structures for further studies. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.039

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