1-(3-bromopropyl)-3-nitro-1H-1,2,4-triazole | 1179774-84-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-(3-bromopropyl)-3-nitro-1H-1,2,4-triazole
• 英文别名: 1-(3-Bromopropyl)-3-nitro-1,2,4-triazole
• CAS: 1179774-84-5
• 化学式: C₅H₇BrN₄O₂
• 分子量: 235.04
• InChiKey: QXYQAZYVZIVAOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  76.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  雷公藤红素 、 1-(3-bromopropyl)-3-nitro-1H-1,2,4-triazole 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以42.3%的产率得到3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid 3-(3-nitro-1H-1,2,4-triazol-1-yl)propyl ester
  参考文献：
  名称：

  Discovery of novel celastrol-triazole derivatives with Hsp90-Cdc37 disruption to induce tumor cell apoptosis

  摘要：

  DOI：

  10.1016/j.bioorg.2021.104867
• 作为产物：
  描述：

  3-硝基-1,2,4-三氮唑 、 1,3-二溴丙烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 72.0h， 生成 1-(3-bromopropyl)-3-nitro-1H-1,2,4-triazole
  参考文献：
  名称：

  Discovery of novel celastrol-triazole derivatives with Hsp90-Cdc37 disruption to induce tumor cell apoptosis

  摘要：

  DOI：

  10.1016/j.bioorg.2021.104867

文献信息

• Novel 3-nitro-1H-1,2,4-triazole-based piperazines and 2-amino-1,3-benzothiazoles as antichagasic agents
  作者：Maria V. Papadopoulou、William D. Bloomer、Howard S. Rosenzweig、Marcel Kaiser、Eric Chatelain、Jean-Robert Ioset

  DOI：10.1016/j.bmc.2013.08.022

  日期：2013.11

  We have previously shown that 3-nitro-1H-1,2,4-triazole-based amines demonstrate significant trypanocidal activity, in particular against Trypanosoma cruzi, the causative parasite of Chagas disease. In the present work we further expanded our research by evaluating in vitro the trypanocidal activity of nitrotriazole-based piperazines and nitrotriazole-based 2-amino-1,3-benzothiazoles to establish additional SARs. All nitrotriazole-based derivatives were active or moderately active against T. cruzi; however two of them did not fulfill the selectivity criteria. Five derivatives were active or moderately active against Trypanosoma brucei rhodesiense while one derivative was moderately active against Leishmania donovani. Active compounds against T. cruzi demonstrated selectivity indexes (toxicity to host cells/toxicity to T. cruzi amastigotes) from 117 to 1725 and 12 of 13 compounds were up to 39-fold more potent than the reference compound benznidazole. Detailed SARs are discussed. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel 3-Nitro-1<i>H</i>-1,2,4-triazole-Based Aliphatic and Aromatic Amines as Anti-Chagasic Agents
  作者：Maria V. Papadopoulou、Bernadette Bourdin Trunz、William D. Bloomer、Caroline McKenzie、Shane R. Wilkinson、Chaiya Prasittichai、Reto Brun、Marcel Kaiser、Els Torreele

  DOI：10.1021/jm201215n

  日期：2011.12.8

  A series of novel 2-nitro-1H-imidazole- and 3-nitro-1H-1,2,4-triazole-based aromatic and aliphatic amines were screened for antitrypanosomal activity and mammalian cytotoxicity by the Drugs for Neglected Diseases initiative (DNDi). Out of 42 compounds tested, 18 3-nitro-1,2,4-triazoles and one 2-nitroimidazole displayed significant growth inhibitory properties against T. cruzi amastigotes (IC50 ranging from 40 nM to 1.97 mu M), without concomitant toxicity toward the host cells (L6 cells), having selectivity indices (SI) 44-1320. Most (16) of these active compounds were up to 33.8-fold more potent than the reference drug benznidazole, tested in parallel. Five novel 3-nitro-1,2,4-triazoles were active against bloodstream-form (BSF) T. b. rhodesiense trypomastigotes (IC50 at nM levels and SI 220-993). An NADH-dependent nitroreductase (TbNTR) plays a role in the antiparasitic activity because BSF T. b. brucei trypomastigotes with elevated TbNTR levels were hypersensitive to tested compounds. Therefore, a novel class of affordable 3-nitro-1,2,4-triazole-based compounds with antitrypanosomal activity has been identified.
• Discovery of novel celastrol-triazole derivatives with Hsp90-Cdc37 disruption to induce tumor cell apoptosis
  作者：Na Li、Cheng Chen、Huiting zhu、Zhixian Shi、Jianbo Sun、Li Chen

  DOI：10.1016/j.bioorg.2021.104867

  日期：2021.6