(3R,5S)-1-[7-amino-2-(trifluoromethyl)-1,8-naphthyridin-4-yl]-5-(hydroxymethyl)pyrrolidin-3-ol | 1413280-63-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (3R,5S)-1-[7-amino-2-(trifluoromethyl)-1,8-naphthyridin-4-yl]-5-(hydroxymethyl)pyrrolidin-3-ol
• CAS: 1413280-63-3
• 化学式: C₁₄H₁₅F₃N₄O₂
• 分子量: 328.294
• InChiKey: AEKITEMPENWBGO-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  7-amino-4-hydroxy-2-trifluoromethyl-1,8-naphthyridine 在 三氯氧磷 作用下， 生成 (3R,5S)-1-[7-amino-2-(trifluoromethyl)-1,8-naphthyridin-4-yl]-5-(hydroxymethyl)pyrrolidin-3-ol
  参考文献：
  名称：

  Structure-guided design, synthesis and biological evaluation of novel DNA ligase inhibitors with in vitro and in vivo anti-staphylococcal activity

  摘要：

  A series of 2-amino-[1,8]-naphthyridine-3-carboxamides (ANCs) with potent inhibition of bacterial NAD+-dependent DNA ligases (LigAs) evolved from a 2,4-diaminopteridine derivative discovered by HTS. The design was guided by several highly resolved X-ray structures of our inhibitors in complex with either Streptococcus pneumoniae or Escherichia coli LigA. The structure-activity-relationship based on the ANC scaffold is discussed. The in-depth characterization of 2-amino-6-bromo-7-(trifluoromethyl)-[1,8]-naphthyridine-3-carboxamide, which displayed promising in vitro (MIC Staphylococcus aureus 1 mg/L) and in vivo anti-staphylococcal activity, is presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.094