2-(1,5-bis(benzyloxy)-4-oxo-1,4-dihydropyridine-2-carboxamido)acetic acid | 1380111-37-4

• 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: 2-(1,5-bis(benzyloxy)-4-oxo-1,4-dihydropyridine-2-carboxamido)acetic acid
• 英文别名: 2-[[4-Oxo-1,5-bis(phenylmethoxy)pyridine-2-carbonyl]amino]acetic acid
• CAS: 1380111-37-4
• 化学式: C₂₂H₂₀N₂O₆
• 分子量: 408.411
• InChiKey: PWSQRQAXIZNSCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(1,5-bis(benzyloxy)-4-oxo-1,4-dihydropyridine-2-carboxamido)acetic acid 在 氢气 、 钯 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 生成 2-((((Z)-1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-((((S)-4-(2-(1,5-dihydroxy-4-oxo-1,4-dihydropyridine-2-carboxamido)acetamido)-2-oxopyrrolidin-1-yl)sulfonyl)carbamoyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid
  参考文献：
  名称：

  Discovery of Efficacious Pseudomonas aeruginosa-Targeted Siderophore-Conjugated Monocarbams by Application of a Semi-mechanistic Pharmacokinetic/Pharmacodynamic Model

  摘要：

  To identify new agents for the treatment of multi-drug-resistant Pseudomonas aeruginosa, we focused on siderophore-conjugated monocarbams. This class of monocyclic beta-lactams are stable to metallo-beta-lactamases and have excellent P. aeruginosa activities due to their ability to exploit the iron uptake machinery of Gram-negative bacteria. Our medicinal chemistry plan focused on identifying a molecule with optimal potency and physical properties and activity for in vivo efficacy. Modifications to the monocarbam linker, siderophore, and oxime portion of the molecules were examined. Through these efforts, a series of pyrrolidinone-based monocarbams with good P. aeruginosa cellular activity (P. aeruginosa MIC90 = 2 mu g/mL), free fraction levels (>20% free), and hydrolytic stability (t(1/2) = 100 h) were identified. To differentiate the lead compounds and enable prioritization for in vivo studies, we applied a semi-mechanistic pharmacokinetic/pharmacodynamic model to enable prediction of in vivo efficacy from in vitro data.

  DOI：

  10.1021/jm501506f
• 作为产物：
  描述：

  Tert-butyl 2-[[4-oxo-1,5-bis(phenylmethoxy)pyridine-2-carbonyl]amino]acetate 在 甲酸 、 碳酸氢钠 作用下， 以 水 、 乙酸乙酯 为溶剂， 生成 2-(1,5-bis(benzyloxy)-4-oxo-1,4-dihydropyridine-2-carboxamido)acetic acid
  参考文献：
  名称：

  [EN] MONOBACTAMS
  [FR] MONOBACTAMES

  摘要：

  本发明涉及一类新的单环内酰胺衍生物及其用于治疗细菌感染的用途。

  公开号：

  WO2012073138A1

文献信息

• Monobactams
  申请人：Pfizer Inc.

  公开号：US20150148326A1

  公开（公告）日：2015-05-28

  The present invention is directed to a new class of monobactam derivatives and their use for treating bacterial infections.