[2-amino-5-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl]methanol | 1413281-40-9

• 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: [2-amino-5-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl]methanol
• CAS: 1413281-40-9
• 化学式: C₁₀H₁₁F₃N₂O
• 分子量: 232.205
• InChiKey: PESYAVBXCJATGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.14
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [2-amino-5-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl]methanol 在 platinum(IV) oxide 、 2-(二甲基氨基)丙酸 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 2-amino-6-cyclopropyl-7-trifluoromethyl-[1,8]naphthyridine-3-carboxylic acid amide
  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
• 作为产物：
  描述：

  ethyl 2-amino-6-(trifluoromethyl)nicotinate 在 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 caesium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 生成 [2-amino-5-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl]methanol
  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