(S)-bis((1-(2-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methyl) 2-(tert-butoxycarbonylamino)pentanedioate | 1507346-56-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-bis((1-(2-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methyl) 2-(tert-butoxycarbonylamino)pentanedioate
• 英文别名: bis[[1-[(2-nitrophenyl)methyl]triazol-4-yl]methyl] (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate
• CAS: 1507346-56-6
• 化学式: C₃₀H₃₃N₉O₁₀
• 分子量: 679.646
• InChiKey: LPZRMBHMIBGFQD-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  49
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  244
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  N-Boc-Glu-propargyl ester 、 2-硝基苄溴 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以87%的产率得到(S)-bis((1-(2-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methyl) 2-(tert-butoxycarbonylamino)pentanedioate
  参考文献：
  名称：

  Synthesis and biological evaluation of amino acid-linked 1,2,3-bistriazole conjugates as potential antimicrobial agents

  摘要：

  A small library of amino acid-linked 1,4-disubstituted 1,2,3-bistriazole conjugates has been synthesized from the N-protected l-amino acids propargyl esters through one-pot click reaction. All the newly synthesized compounds were tested in vitro for antimicrobial activity against Gram-positive (Staphylococcus aureus, Bacillus subtilis), Gram-negative (Escherichia coli) bacteria and fungi (Candida albicans, Aspergillus niger). The antibacterial evaluation data indicated that compounds 3c, 3h, 5a, 5b, 5c, 5d, 5e, 5g, and 5h exhibited comparable activity to standard ciprofloxacin. However, the bistriazoles 3b, 3c, 3e, 3f, and 3g showed good antifungal activity than others against both fungi. Further, docking simulation of the two most active compounds 5c against S. aureus tyrosyl tRNA synthetase and 5h into E. coli topoisomerase II DNA Gyrase B, respectively, was also performed.

  DOI：

  10.1007/s00044-013-0882-z

文献信息

• Synthesis and biological evaluation of amino acid-linked 1,2,3-bistriazole conjugates as potential antimicrobial agents
  作者：C. P. Kaushik、Kashmiri Lal、Ashwani Kumar、Sunil Kumar

  DOI：10.1007/s00044-013-0882-z

  日期：2014.6

  A small library of amino acid-linked 1,4-disubstituted 1,2,3-bistriazole conjugates has been synthesized from the N-protected l-amino acids propargyl esters through one-pot click reaction. All the newly synthesized compounds were tested in vitro for antimicrobial activity against Gram-positive (Staphylococcus aureus, Bacillus subtilis), Gram-negative (Escherichia coli) bacteria and fungi (Candida albicans, Aspergillus niger). The antibacterial evaluation data indicated that compounds 3c, 3h, 5a, 5b, 5c, 5d, 5e, 5g, and 5h exhibited comparable activity to standard ciprofloxacin. However, the bistriazoles 3b, 3c, 3e, 3f, and 3g showed good antifungal activity than others against both fungi. Further, docking simulation of the two most active compounds 5c against S. aureus tyrosyl tRNA synthetase and 5h into E. coli topoisomerase II DNA Gyrase B, respectively, was also performed.