(2R)-2-methyl-2-(methylsulfonyl)-4-(2'-oxo-2,4'-bipyridin-1'(2'H)-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide | 1358778-58-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (2R)-2-methyl-2-(methylsulfonyl)-4-(2'-oxo-2,4'-bipyridin-1'(2'H)-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide
• 英文别名: (2R)-2-methyl-2-methylsulfonyl-N-(oxan-2-yloxy)-4-(2-oxo-4-pyridin-2-ylpyridin-1-yl)butanamide
• CAS: 1358778-58-1
• 化学式: C₂₁H₂₇N₃O₆S
• 分子量: 449.528
• InChiKey: FLBBCSBOKOZZPA-VGAJERRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R)-2-methyl-2-(methylsulfonyl)-4-(2'-oxo-2,4'-bipyridin-1'(2'H)-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide 在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 以72%的产率得到(2R)-N-hydroxy-2-methyl-2-(methylsulfonyl)-4-(2'-oxo-2,4'-bipyridin-1'(2'H)-yl)butanamide hydrochloride
  参考文献：
  名称：

  Pyridone Methylsulfone Hydroxamate LpxC Inhibitors for the Treatment of Serious Gram-Negative Infections

  摘要：

  The synthesis and biological activity of a new series of LpxC inhibitors represented by pyridone methylsulfone hydroxamate 2a is presented. Members of this series have improved solubility and free fraction when compared to compounds in the previously described biphenyl methylsulfone hydroxamate series, and they maintain superior Gram-negative antibacterial activity to comparator agents.

  DOI：

  10.1021/jm2014875
• 作为产物：
  描述：

  (R)-ethyl 4-bromo-2-methyl-2-(methylsulfonyl)butanoate 在 N-甲基吗啉 、 四(三苯基膦)钯 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 、 四丁基碘化铵 、 caesium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 、 甲醇 、 水 、 叔丁醇 为溶剂， 反应 73.0h， 生成 (2R)-2-methyl-2-(methylsulfonyl)-4-(2'-oxo-2,4'-bipyridin-1'(2'H)-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide
  参考文献：
  名称：

  Pyridone Methylsulfone Hydroxamate LpxC Inhibitors for the Treatment of Serious Gram-Negative Infections

  摘要：

  The synthesis and biological activity of a new series of LpxC inhibitors represented by pyridone methylsulfone hydroxamate 2a is presented. Members of this series have improved solubility and free fraction when compared to compounds in the previously described biphenyl methylsulfone hydroxamate series, and they maintain superior Gram-negative antibacterial activity to comparator agents.

  DOI：

  10.1021/jm2014875