((2S,3S)-3-((Z)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-(phenoxyimino)acetamido)-4-oxoazetidin-2-yl)methyl 4-methylbenzenesulfonate | 1445727-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: ((2S,3S)-3-((Z)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-(phenoxyimino)acetamido)-4-oxoazetidin-2-yl)methyl 4-methylbenzenesulfonate
• CAS: 1445727-80-9
• 化学式: C₂₇H₂₉N₅O₈S₂
• 分子量: 615.688
• InChiKey: JASTXTILYROFKR-XXYMXONASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  174.38
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  ((2S,3S)-3-((Z)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-(phenoxyimino)acetamido)-4-oxoazetidin-2-yl)methyl 4-methylbenzenesulfonate 在 四丁基碘化铵 作用下， 以 四氢呋喃 为溶剂， 反应 41.0h， 以80%的产率得到tert-butyl (4-((Z)-2-(((2R,3S)-2-(azidomethyl)-4-oxoazetidin-3-yl)amino)-2-oxo-1-(phenoxyimino)ethyl)thiazol-2-yl)carbamate
  参考文献：
  名称：

  Pyridone-Conjugated Monobactam Antibiotics with Gram-Negative Activity

  摘要：

  Herein we describe the structure-aided design and synthesis of a series of pyridone-conjugated monohactam analogues with in vitro, antibacterial activity against clinically relevant Grain-negative species including Pseuedomonas aeruginosa, Klebsiella pneumoniae, and Escherichia coli. Rat pharmacokinetic studies with,compound 17 demonstrate low clearance and low plasma protein binding. In addition evidence is provided for a number of analogues suggesting that the siderophore receptors PiuA and PirA play a role in drug uptake in P. aeruginosa strain PAO1.

  DOI：

  10.1021/jm400560z
• 作为产物：
  描述：

  Tert-butyl 4-(2-ethoxy-2-oxoacetyl)-2-[(2-methylpropan-2-yl)oxycarbonylimino]-1,3-thiazole-3-carboxylate 在 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 ((2S,3S)-3-((Z)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-(phenoxyimino)acetamido)-4-oxoazetidin-2-yl)methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Pyridone-Conjugated Monobactam Antibiotics with Gram-Negative Activity

  摘要：

  Herein we describe the structure-aided design and synthesis of a series of pyridone-conjugated monohactam analogues with in vitro, antibacterial activity against clinically relevant Grain-negative species including Pseuedomonas aeruginosa, Klebsiella pneumoniae, and Escherichia coli. Rat pharmacokinetic studies with,compound 17 demonstrate low clearance and low plasma protein binding. In addition evidence is provided for a number of analogues suggesting that the siderophore receptors PiuA and PirA play a role in drug uptake in P. aeruginosa strain PAO1.

  DOI：

  10.1021/jm400560z