N-((1-(3-hydroxy-4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)-5-nitrofuran-2-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-((1-(3-hydroxy-4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)-5-nitrofuran-2-carboxamide
• 英文别名: N-[[1-[(3-hydroxy-4-methoxyphenyl)methyl]triazol-4-yl]methyl]-5-nitrofuran-2-carboxamide
• 化学式: C₁₆H₁₅N₅O₆
• 分子量: 373.325
• InChiKey: ZGTNFEWBHGLPOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-hydroxy-4-methoxybenzyl bromide 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 20.0h， 生成 N-((1-(3-hydroxy-4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)-5-nitrofuran-2-carboxamide
  参考文献：
  名称：

  Anti-tubercular agents. Part 8: Synthesis, antibacterial and antitubercular activity of 5-nitrofuran based 1,2,3-triazoles

  摘要：

  A series of 5-nitrofuran-triazole conjugates were synthesized and evaluated for their antimicrobial activity against both Gram-positive and Gram-negative bacterial strains. All the compounds exhibited promising inhibition towards Gram-positive pathogenic strains, while mild inhibitory effects were observed towards Gram-negative bacterial strains. Some of the compounds 8a, 8b, 8e, 8f, 8h are most active among the series exhibiting MIC value of 1.17 mu g/ml against different bacterial strains. The bactericidal activity is found to be in accordance with the bacterial growth inhibition data. Compound 8e was found to be equipotent to the standard drug Ciprofloxacin displaying MBC value of 1.17 mu g/ml against the bacterial strain Bacillus subtilis. The compounds have also demonstrated promising antibacterial activity against the resistant strain MRSA and were found to be effective inhibitors of biofilm formation. The compound 8b exhibited excellent anti-biofilm activity with IC50 value as low as 0.8 mu g/ml. These conjugates were also screened for antitubercular activity against Mycobacterium tuberculosis H(37)Rv strain. Compound 8e showed promising antitubercular activity with MIC value of 0.25 mu g/ml. Most of these compounds are less toxic to normal mammalian cells than the widely used antibacterial drug Ciprofloxacin. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.010

文献信息

• Anti-tubercular agents. Part 8: Synthesis, antibacterial and antitubercular activity of 5-nitrofuran based 1,2,3-triazoles
  作者：Ahmed Kamal、Syed Mohammed Ali Hussaini、Shaikh Faazil、Y. Poornachandra、G. Narender Reddy、C. Ganesh Kumar、Vikrant Singh Rajput、Chitra Rani、Rashmi Sharma、Inshad Ali Khan、N. Jagadeesh Babu

  DOI：10.1016/j.bmcl.2013.10.010

  日期：2013.12

  A series of 5-nitrofuran-triazole conjugates were synthesized and evaluated for their antimicrobial activity against both Gram-positive and Gram-negative bacterial strains. All the compounds exhibited promising inhibition towards Gram-positive pathogenic strains, while mild inhibitory effects were observed towards Gram-negative bacterial strains. Some of the compounds 8a, 8b, 8e, 8f, 8h are most active among the series exhibiting MIC value of 1.17 mu g/ml against different bacterial strains. The bactericidal activity is found to be in accordance with the bacterial growth inhibition data. Compound 8e was found to be equipotent to the standard drug Ciprofloxacin displaying MBC value of 1.17 mu g/ml against the bacterial strain Bacillus subtilis. The compounds have also demonstrated promising antibacterial activity against the resistant strain MRSA and were found to be effective inhibitors of biofilm formation. The compound 8b exhibited excellent anti-biofilm activity with IC50 value as low as 0.8 mu g/ml. These conjugates were also screened for antitubercular activity against Mycobacterium tuberculosis H(37)Rv strain. Compound 8e showed promising antitubercular activity with MIC value of 0.25 mu g/ml. Most of these compounds are less toxic to normal mammalian cells than the widely used antibacterial drug Ciprofloxacin. (C) 2013 Elsevier Ltd. All rights reserved.