tert-butyl 2-[(Z)-[2-[[(2R,3S)-2-[[[4,5-bis(phenylmethoxy)pyridine-2-carbonyl]amino]methyl]-4-oxoazetidin-3-yl]amino]-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-oxoethylidene]amino]oxy-2-methylpropanoate | 1380110-54-2

• 英文名称: tert-butyl 2-[(Z)-[2-[[(2R,3S)-2-[[[4,5-bis(phenylmethoxy)pyridine-2-carbonyl]amino]methyl]-4-oxoazetidin-3-yl]amino]-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-oxoethylidene]amino]oxy-2-methylpropanoate
• CAS: 1380110-54-2
• 化学式: C₄₂H₄₉N₇O₁₀S
• 分子量: 843.958
• InChiKey: FBJFWUCFXCJZQE-WJUMPTGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  60
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  246
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[(Z)-[2-[[(2R,3S)-2-[[[4,5-bis(phenylmethoxy)pyridine-2-carbonyl]amino]methyl]-4-oxoazetidin-3-yl]amino]-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-oxoethylidene]amino]oxy-2-methylpropanoate 在 三氧化硫吡啶 、 三氯化硼 作用下， 以 二氯甲烷 、 对二甲苯 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-({[(1Z)-1-(2-amino-1,3-thiazol-4-yl)-2-{[(2R,3S)-2-({[(5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)carbonyl]amino}methyl)-4-oxo-1-sulfoazetidin-3-yl]amino}-2-oxoethylidene]amino}oxy)-2-methylpropanoic acid
  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：

  (Z)-tert-butyl 2-(((1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-((2,5-dioxopyrrolidin-1-yl)oxy)-2-oxoethylidene)amino)oxy)-2-methylpropanoate 在 咪唑 、 palladium 10% on activated carbon 、 碘 、 叠氮化四丁基铵 、 碳酸氢钠 、 三乙胺 、 三苯基膦 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 20.0~35.0 ℃ 、206.85 kPa 条件下， 反应 54.08h， 生成 tert-butyl 2-[(Z)-[2-[[(2R,3S)-2-[[[4,5-bis(phenylmethoxy)pyridine-2-carbonyl]amino]methyl]-4-oxoazetidin-3-yl]amino]-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-oxoethylidene]amino]oxy-2-methylpropanoate
  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