N-(adamantan-1-yl)-2-(1-oxoisoindolin-2-yl)acetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(adamantan-1-yl)-2-(1-oxoisoindolin-2-yl)acetamide
• 英文别名: N-(1-adamantyl)-2-(3-oxo-1H-isoindol-2-yl)acetamide
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: KFEAAVDNNHTWHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1-氧代-1,3-二氢-异吲哚-2-基)-乙酸 、 盐酸金刚烷胺 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 70.0h， 以31%的产率得到N-(adamantan-1-yl)-2-(1-oxoisoindolin-2-yl)acetamide
  参考文献：
  名称：

  Discovery and structure–activity relationship studies of irreversible benzisothiazolinone-based inhibitors against Staphylococcus aureus sortase A transpeptidase

  摘要：

  Gram-positive bacteria, in general, and staphylococci, in particular, are the widespread cause of nosocomial and community-acquired infections. The rapid evolvement of strains resistant to antibiotics currently in use is a serious challenge. Novel antimicrobial compounds have to be developed to fight these resistant bacteria, and sortase A, a bacterial cell wall enzyme, is a promising target for novel therapies. As a transpeptidase that covalently attaches various virulence factors to the cell surface, this enzyme plays a crucial role in the ability of bacteria to invade the host's tissues and to escape the immune response. In this study we have screened a small molecule library against recombinant Staphylococcus aureus sortase A using an in vitro FRET-based assay. The selected hits were validated by NMR methods in order to exclude false positives and to analyze the reversibility of inhibition. Further structural and functional analysis of the best hit allowed the identification of a novel class of benzisothiazolinone-based compounds as potent and promising sortase inhibitors. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.011