(4-acetylamino-2,3-dihydro-3-oxo-4H-1,2,4-triazol-2-yl)acetate de tert-butyle | 143677-56-9

• 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: (4-acetylamino-2,3-dihydro-3-oxo-4H-1,2,4-triazol-2-yl)acetate de tert-butyle
• 英文别名: Tert-butyl 2-(4-acetamido-5-oxo-1,2,4-triazol-1-yl)acetate；tert-butyl 2-(4-acetamido-5-oxo-1,2,4-triazol-1-yl)acetate
• CAS: 143677-56-9
• 化学式: C₁₀H₁₆N₄O₄
• 分子量: 256.261
• InChiKey: MJLBNJDJDJECOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-acetylamino-2,3-dihydro-3-oxo-4H-1,2,4-triazol-2-yl)acetate de tert-butyle 在 三氟乙酸 作用下， 以 硝基甲烷 为溶剂， 反应 0.25h， 以94%的产率得到acide (4-acetylamino-2,3-dihydro-3-oxo-4H-1,2,4-triazol-2-yl)acetique
  参考文献：
  名称：

  Synthèse, étude théorique et évaluation biologique de dérivés du 4-amino-4H-1,2,4-triazole analogues des antibiotiques β-lactamiques

  摘要：

  The synthesis of three classes of potential antibiotic compounds derived from 4-amino-4H- 1,2,4-triazole and related to beta-lactam antibiotics is described. Their originality belongs to the replacement of the beta-lactam carbonyl moiety by another electrophilic centre of the same sp2 geometry. As a result, their interaction with the bacterial target enzyme might lead to the formation of a covalent complex different from the classical acylenzyme. A theoretical study of their structural analogy and their reactivity compared to those of a model beta-lactam justifies their interest in the present context. However, the actual biological results indicate a lack of antibacterial activity.

  DOI：

  10.1016/0223-5234(92)90003-j
• 作为产物：
  描述：

  bromure de 4-amino-1-tert-butoxycarbonylmethyl-4H-1,2,4-triazolium 在 sodium hydroxide 、 三乙胺 作用下， 以 吡啶 为溶剂， 反应 49.42h， 生成 (4-acetylamino-2,3-dihydro-3-oxo-4H-1,2,4-triazol-2-yl)acetate de tert-butyle
  参考文献：
  名称：

  Synthèse, étude théorique et évaluation biologique de dérivés du 4-amino-4H-1,2,4-triazole analogues des antibiotiques β-lactamiques

  摘要：

  The synthesis of three classes of potential antibiotic compounds derived from 4-amino-4H- 1,2,4-triazole and related to beta-lactam antibiotics is described. Their originality belongs to the replacement of the beta-lactam carbonyl moiety by another electrophilic centre of the same sp2 geometry. As a result, their interaction with the bacterial target enzyme might lead to the formation of a covalent complex different from the classical acylenzyme. A theoretical study of their structural analogy and their reactivity compared to those of a model beta-lactam justifies their interest in the present context. However, the actual biological results indicate a lack of antibacterial activity.

  DOI：

  10.1016/0223-5234(92)90003-j

文献信息

• Synthèse, étude théorique et évaluation biologique de dérivés du 4-amino-4H-1,2,4-triazole analogues des antibiotiques β-lactamiques
  作者：B Pirotte、G Dive、J Delarge、B Masereel、L Dupont、L Thunus、M Schynts、J Coyette、JM Frère

  DOI：10.1016/0223-5234(92)90003-j

  日期：1992.4

  The synthesis of three classes of potential antibiotic compounds derived from 4-amino-4H- 1,2,4-triazole and related to beta-lactam antibiotics is described. Their originality belongs to the replacement of the beta-lactam carbonyl moiety by another electrophilic centre of the same sp2 geometry. As a result, their interaction with the bacterial target enzyme might lead to the formation of a covalent complex different from the classical acylenzyme. A theoretical study of their structural analogy and their reactivity compared to those of a model beta-lactam justifies their interest in the present context. However, the actual biological results indicate a lack of antibacterial activity.