1-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)-4-(hydroxymethyl)-1H-1,2,3-triazole | 1144040-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)-4-(hydroxymethyl)-1H-1,2,3-triazole
• 英文别名: (1-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)-1H-1,2,3-triazol-4-yl)methanol；{1-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl]-1H-[1,2,3]triazol-4-yl}-methanol；1-[2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl]-1H-1,2,3-triazole-4-methanol；[1-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]triazol-4-yl]methanol
• CAS: 1144040-15-2
• 化学式: C₉H₁₂N₆O₃
• mdl: MFCD17338485
• 分子量: 252.233
• InChiKey: GVFLROSLXOQKRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)-4-(hydroxymethyl)-1H-1,2,3-triazole 、 对氟苯甲醛 在 sodium methylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 12.0h， 以57%的产率得到(E)-(1-(2-(2-(4-fluorostyryl)-5-nitro-1H-imidazol-1-yl)ethyl)-1H-1,2,3-triazol-4-yl)methanol
  参考文献：
  名称：

  Synthesis, antiamoebic activity and docking studies of metronidazole-triazole-styryl hybrids

  摘要：

  A series of 22 novel metronidazole-triazole-styryl hybrids were synthesized and evaluated for their in vitro antiamoebic activity against HM1: IMSS strain of Entamoeba histolytica. Some of the hybrids were found to be more active (IC50 = 0.12-035 mu M) than the reference drug metronidazole (IC50=1.79 mu M). The most active compounds were found to be non-toxic (up to 50 mu M) against the Vero cells showing a good safety profile of these hybrids. The docking and ADMET studies were also conducted to investigate the probable mode of action. Docking studies showed significant binding affinity in the active site of E. histolytica thioredoxin reductase (EhTrR) protein. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.03.033
• 作为产物：
  描述：

  甲硝唑 在 sodium azide 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 1-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)-4-(hydroxymethyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  甲硝唑与丁子香酚类似物杂交合成新型杀锥虫剂

  摘要：

  硝基咪唑化合物是众所周知的生物活性物质，并且已经报道了结构活性关系，其中硝基在咪唑环内的位置对其活性有很大影响。本研究的重点是通过甲硝唑与不同天然酚（丁子香酚、二氢丁子香酚和愈创木酚）的杂交来合成新的杀锥虫剂。为了分析连接器对生物活性的影响，我们探索了两种不同的偶联方法：i）经典的直接酯化（AD 化合物）和 ii）使用三唑连接器（AC 化合物）的“点击”化学。

  DOI：

  10.1016/j.bioorg.2024.107288

文献信息

• Synthesis and antibacterial activity evaluation of metronidazole–triazole conjugates
  作者：Beena、Nitin Kumar、Rajesh K. Rohilla、N. Roy、Diwan S. Rawat

  DOI：10.1016/j.bmcl.2009.01.037

  日期：2009.3

  Synthesis and antibacterial activity of metronidazole-triazole conjugates are reported. Total 21 hybrid compounds have been synthesized with different substitution pattern on the triazole ring in order to study their influence on the antibacterial activity. These compounds demonstrated potent to weak antibacterial activity against Gram-positive, and Gram-negative bacteria. Six compounds have shown equal or better antibacterial activity against Gram-negative strains than the reference compound. (C) 2009 Elsevier Ltd. All rights reserved.
• Metronidazole-triazole conjugates: Activity against Clostridium difficile and parasites
  作者：Angie M. Jarrad、Tomislav Karoli、Anjan Debnath、Chin Yen Tay、Johnny X. Huang、Geraldine Kaeslin、Alysha G. Elliott、Yukiko Miyamoto、Soumya Ramu、Angela M. Kavanagh、Johannes Zuegg、Lars Eckmann、Mark A.T. Blaskovich、Matthew A. Cooper

  DOI：10.1016/j.ejmech.2015.06.019

  日期：2015.8

  Metronidazole has been used clinically for over 50 years as an antiparasitic and broad-spectrum antibacterial agent effective against anaerobic bacteria. However resistance to metronidazole in parasites and bacteria has been reported, and improved second-generation metronidazole analogues are needed. The copper catalysed Huigsen azide-alkyne 1,3-dipolar cycloaddition offers a way to efficiently assemble new libraries of metronidazole analogues. Several new metronidazole-triazole conjugates (Mtz-triazoles) have been identified with excellent broad spectrum antimicrobial and antiparasitic activity targeting Clostridium difficile, Entamoeba histolytica and Giardia lambda. Cross resistance to metronidazole was observed against stable metronidazole resistant C. difficile and G.. lamblia strains. However for the most potent Mtz-triazoles, the activity remained in a therapeutically relevant window. (C) 2015 The Authors. Published by Elsevier Masson SAS. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).