2-(4-phenyl-1H-1,2,3-triazol-1-yl)-1,4-naphthoquinone | 1353244-45-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-phenyl-1H-1,2,3-triazol-1-yl)-1,4-naphthoquinone
• 英文别名: 2-(4-Phenyltriazol-1-yl)naphthalene-1,4-dione
• CAS: 1353244-45-7
• 化学式: C₁₈H₁₁N₃O₂
• 分子量: 301.304
• InChiKey: JEJKJYMUGNKXFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.8
• 氢给体数：
  0
• 氢受体数：
  4

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-(4-phenyl-1H-1,2,3-triazol-1-yl)-1,4-naphthoquinone
  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
• Synthesis and anti-Trypanosoma cruzi activity of naphthoquinone-containing triazoles: Electrochemical studies on the effects of the quinoidal moiety
  作者：Emilay B.T. Diogo、Gleiston G. Dias、Bernardo L. Rodrigues、Tiago T. Guimarães、Wagner O. Valença、Celso A. Camara、Ronaldo N. de Oliveira、Mauro G. da Silva、Vitor F. Ferreira、Yen Galdino de Paiva、Marilia O.F. Goulart、Rubem F.S. Menna-Barreto、Solange L. de Castro、Eufrânio N. da Silva Júnior

  DOI：10.1016/j.bmc.2013.08.055

  日期：2013.11

  In our continued search for novel trypanocidal compounds, twenty-six derivatives of para-and orthonaphthoquinones coupled to 1,2,3-triazoles were synthesized. These compounds were evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological agent of Chagas disease. Compounds 17-24, 28-30 and 36-38 are described herein for the first time. Three of these novel compounds (28-30) were found to be more potent than the standard drug benznidazole, with IC50/24 h values between 6.8 and 80.8 mu M. Analysis of the toxicity to heart muscle cells led to LC50/24 h of <125, 63.1 and 281.6 mu M for 28, 29 and 30, respectively. Displaying a selectivity index of 34.3, compound 30 will be further evaluated in vivo. The electrochemical properties of selected compounds were evaluated in an attempt to find correlations with trypanocidal activity, and it was observed that more electrophilic quinones were generally more potent. (C) 2013 Elsevier Ltd. All rights reserved.
• 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
  作者：Eufrânio N. da Silva、Isadora M.M. de Melo、Emilay B.T. Diogo、Verenice A. Costa、José D. de Souza Filho、Wagner O. Valença、Celso A. Camara、Ronaldo N. de Oliveira、Alexandre S. de Araujo、Flávio S. Emery、Marcelo R. dos Santos、Carlos A. de Simone、Rubem F.S. Menna-Barreto、Solange L. de Castro

  DOI：10.1016/j.ejmech.2012.03.039

  日期：2012.6

  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.
• 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
  作者：Tiago T. Guimarães、Maria do Carmo F.R. Pinto、Juliane S. Lanza、Maria N. Melo、Rubens L. do Monte-Neto、Isadora M.M. de Melo、Emilay B.T. Diogo、Vitor F. Ferreira、Celso A. Camara、Wagner O. Valença、Ronaldo N. de Oliveira、Frédéric Frézard、Eufrânio N. da Silva Júnior

  DOI：10.1016/j.ejmech.2013.02.038

  日期：2013.5

  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.