1-(4-nitrobenzyl)-4-((naphthalen-6-yloxy)methyl)-1H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(4-nitrobenzyl)-4-((naphthalen-6-yloxy)methyl)-1H-1,2,3-triazole
• 英文别名: 4-((naphthalen-2-yloxy)methyl)-1-(4-nitrobenzyl)-1H-1,2,3-triazole；4-((Naphthalen-2-yloxy)methyl)-1-(4-nitrobenzyl)-1h-1,2,3-triazole；4-(naphthalen-2-yloxymethyl)-1-[(4-nitrophenyl)methyl]triazole
• 化学式: C₂₀H₁₆N₄O₃
• 分子量: 360.372
• InChiKey: YKPAYYBJDLLTJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  85.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-萘酚 在 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 15.5h， 生成 1-(4-nitrobenzyl)-4-((naphthalen-6-yloxy)methyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis and evaluation of naphthyl bearing 1,2,3-triazole analogs as antiplasmodial agents, cytotoxicity and docking studies

  摘要：

  Novel series of naphthyl bearing 1,2,3-triazoles (4a-t) were synthesized and evaluated for their in vitro antiplasmodial activity against pyrimethamine (Pyr)-sensitive and resistant strains of Plasmodium falciparum. The synthesized compounds were assessed for their cytotoxicity employing human embryonic kidney cell line (HEK-293), and none of them was found to be toxic. Among them 4j, 4k, 4l, 4m, 4n, 4t exhibited significant antiplasmodial activity in both strains, of which compounds 4m, 4n and 4t (similar to 3.0fold) displayed superior activity to Pyr against resistant strain. Pyr and selected compounds (4n, 4p and 4t) that repressed parasite development also inhibited PfDHFR activity of the soluble parasite extract, suggesting that anti-parasitic activity of these compounds is a result of inhibition of the parasite DHFR. In silico studies suggest that activity of these compounds might be enhanced due to p-p stacking. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.10.029

文献信息

• Dendrimer-encapsulated copper(II) immobilized on Fe3O4@SiO2 NPs: a robust recoverable catalyst for click synthesis of 1,2,3-triazole derivatives in water under mild conditions
  作者：Ali Reza Sardarian、Fattah Mohammadi、Mohsen Esmaeilpour

  DOI：10.1007/s11164-018-3672-x

  日期：2019.3

  In this paper, we have introduced Fe3O4@SiO2-dendrimer-encapsulated Cu(II) as a heterogeneous reusable catalyst for Cu-catalyzed azide-alkyne cycloaddition (CuAAC) reaction in good to excellent yields at ambient temperature in water without requiring ligands, reducing agents and bases. This present methodology is a clean, and environmentally friendly approach that offers many advantages including excellent yields, operational simplicity, short reaction time, and absence of any tedious workup or purification. Moreover, of interesting features are the stability of the catalyst toward leaching and the possibility of catalyst recycling without any significant loss of activity. In this paper, we have introduced Fe3O4@SiO2-dendrimer-encapsulated Cu(II) as a heterogeneous reusable catalyst for Cu-catalyzed azide-alkyne cycloaddition reaction (CuAAC) in good to excellent yields at ambient temperature in water without requiring ligands, reducing agents and bases.

  本文中，我们介绍了Fe3O4@SiO2-树枝状聚合物包裹的铜(II)作为一种异相可再利用催化剂，用于在水相中室温下进行的铜催化的叠氮-炔环加成反应（CuAAC），无需使用配体、还原剂和碱，即可获得良好至优异的产率。目前的方法是一种清洁、环境友好的途径，具有许多优点，包括优异的产率、操作简便、反应时间短，且无需繁琐的后处理或纯化步骤。此外，该催化剂的一个有趣特性是其抗浸出稳定性以及催化剂回收时不显著损失活性的可能性。在本文中，我们介绍了Fe3O4@SiO2-树枝状聚合物包裹的铜(II)作为一种异相可再利用催化剂，用于在水相中室温下进行的铜催化的叠氮-炔环加成反应（CuAAC），无需使用配体、还原剂和碱，即可获得良好至优异的产率。
• Synthesis and evaluation of naphthyl bearing 1,2,3-triazole analogs as antiplasmodial agents, cytotoxicity and docking studies
  作者：Saikrishna Balabadra、MeenaKumari Kotni、Vijjulatha Manga、Aparna Devi Allanki、Rajesh Prasad、Puran Singh Sijwali

  DOI：10.1016/j.bmc.2016.10.029

  日期：2017.1

  Novel series of naphthyl bearing 1,2,3-triazoles (4a-t) were synthesized and evaluated for their in vitro antiplasmodial activity against pyrimethamine (Pyr)-sensitive and resistant strains of Plasmodium falciparum. The synthesized compounds were assessed for their cytotoxicity employing human embryonic kidney cell line (HEK-293), and none of them was found to be toxic. Among them 4j, 4k, 4l, 4m, 4n, 4t exhibited significant antiplasmodial activity in both strains, of which compounds 4m, 4n and 4t (similar to 3.0fold) displayed superior activity to Pyr against resistant strain. Pyr and selected compounds (4n, 4p and 4t) that repressed parasite development also inhibited PfDHFR activity of the soluble parasite extract, suggesting that anti-parasitic activity of these compounds is a result of inhibition of the parasite DHFR. In silico studies suggest that activity of these compounds might be enhanced due to p-p stacking. (C) 2016 Elsevier Ltd. All rights reserved.