2-[3-[4-[[(1,4-Dioxonaphthalen-2-yl)amino]methyl]triazol-1-yl]propyl]isoindole-1,3-dione | 1426338-64-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[3-[4-[[(1,4-Dioxonaphthalen-2-yl)amino]methyl]triazol-1-yl]propyl]isoindole-1,3-dione
• 英文别名: 2-[3-[4-[[(1,4-dioxonaphthalen-2-yl)amino]methyl]triazol-1-yl]propyl]isoindole-1,3-dione
• CAS: 1426338-64-8
• 化学式: C₂₄H₁₉N₅O₄
• 分子量: 441.446
• InChiKey: AOJPJSCXOCMBEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(丙-2-炔-1-基氨基)萘-1,4-二酮 、 2-(3-叠氮丙基)异吲哚-1,3-二酮 在 copper(l) iodide 作用下， 以 乙腈 为溶剂， 生成 2-[3-[4-[[(1,4-Dioxonaphthalen-2-yl)amino]methyl]triazol-1-yl]propyl]isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis and anti-Trypanosoma cruzi activity of naphthoquinone-containing triazoles: Electrochemical studies on the effects of the quinoidal moiety

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2013.08.055

文献信息

• Synthesis of N-substituted phthalimidoalkyl 1H-1,2,3-triazoles: a molecular diversity combining click chemistry and ultrasound irradiation
  作者：Moara T. da Silva、Ronaldo N. de Oliveira、Wagner O. Valença、Fernanda C. G. Barbosa、Mauro G. da Silva、Celso A. Camara

  DOI：10.1590/s0103-50532012005000053

  日期：——

  A series of 1,2,3-triazole derivatives was synthesized from N-phthalimidoalkyl-azides (A(1)-A(4)) and alkynes (a-e) under ultrasound irradiation in the presence of CuI, Et3N and DMF as solvent. The present protocol afforded 18 new 1,2,3-triazoles (1-4) in good-to-excellent yields (67-98%).
• 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.