4-((2-bromonaphthalen-6-yloxy)methyl)-1-allyl-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: 4-((2-bromonaphthalen-6-yloxy)methyl)-1-allyl-1H-1,2,3-triazole
• 英文别名: 4-[(6-Bromonaphthalen-2-yl)oxymethyl]-1-prop-2-enyltriazole；4-[(6-bromonaphthalen-2-yl)oxymethyl]-1-prop-2-enyltriazole
• 化学式: C₁₆H₁₄BrN₃O
• 分子量: 344.211
• InChiKey: QEXDUPARKYCPRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-溴-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 4-((2-bromonaphthalen-6-yloxy)methyl)-1-allyl-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

• 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.