iodure de 4-amino-2-tert-butoxycarbonylmethyl-3-(methylthio)-4H-1,2,4-triazolium | 143677-49-0

• 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: iodure de 4-amino-2-tert-butoxycarbonylmethyl-3-(methylthio)-4H-1,2,4-triazolium
• 英文别名: Tert-butyl 2-(4-amino-5-methylsulfanyl-1,2,4-triazol-4-ium-1-yl)acetate;iodide
• CAS: 143677-49-0
• 化学式: C₉H₁₇N₄O₂S*I
• 分子量: 372.23
• InChiKey: GGMKCZRRLIUQDS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.05
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  99.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  iodure de 4-amino-2-tert-butoxycarbonylmethyl-3-(methylthio)-4H-1,2,4-triazolium 在 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.17h， 生成 <4-bis<2Z-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetyl>amino-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
• 作为产物：
  描述：

  bromure de 4-amino-1-tert-butoxycarbonylmethyl-4H-1,2,4-triazolium 在 三乙胺 作用下， 以 吡啶 为溶剂， 反应 48.25h， 生成 iodure de 4-amino-2-tert-butoxycarbonylmethyl-3-(methylthio)-4H-1,2,4-triazolium
  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.