propionic acid 1-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl]-1H-[1,2,3]trirazol-4-ylmethyl ester | 1144040-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: propionic acid 1-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl]-1H-[1,2,3]trirazol-4-ylmethyl ester
• 英文别名: {1-[2-(2-methyl-5-nitro-imidazol-1-yl)ethyl]-1H-[1,2,3]triazol-4-yl}methyl propanoate；[1-[2-(2-Methyl-5-nitroimidazol-1-yl)ethyl]triazol-4-yl]methyl propanoate
• CAS: 1144040-17-4
• 化学式: C₁₂H₁₆N₆O₄
• 分子量: 308.297
• InChiKey: XJOWXEGNOWMKNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  甲硝唑 在 吡啶 、 sodium azide 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 15.0h， 生成 propionic acid 1-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl]-1H-[1,2,3]trirazol-4-ylmethyl ester
  参考文献：
  名称：

  Anti-methicillin resistant Staphylococcus aureus activity, synergism with oxacillin and molecular docking studies of metronidazole-triazole hybrids

  摘要：

  MRSA causes 60-70% of Staphylococcus aureus infection in hospitals and it has developed resistance against the currently available drugs. Interestingly, a series of 35 metronidazole-triazole hybrids on screening against MRSA were found to be active. Compound 22 was found to be effective at 4 mu g/mL concentration against nine strains of MRSA. The inhibitory activity was further enhanced upto 1 mu g/mL when this compound was used in combination with oxacillin in 1:1 ratio. All the compounds were found to be non-toxic in THP-1 cell line upto a concentration of 50 mu M. The time-kill kinetics studies suggested bacteriostatic nature of the compounds. In silico studies show that these compounds interact with Thr600, Ser598, Asn464, His583 and Tyr446 in the active site of PBP2a crystal structure from MRSA. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.041

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.