7-amino-4-hydroxy-2-trifluoromethyl-1,8-naphthyridine | 210643-04-2

• 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: 7-amino-4-hydroxy-2-trifluoromethyl-1,8-naphthyridine
• 英文别名: 7-amino-2-(trifluoromethyl)-1H-1,8-naphthyridin-4-one
• CAS: 210643-04-2
• 化学式: C₉H₆F₃N₃O
• 分子量: 229.161
• InChiKey: TUYYLOSMNNYELL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  68
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-amino-4-hydroxy-2-trifluoromethyl-1,8-naphthyridine 在 ammonium hydroxide 、 sodium hydroxide 、 硫酸 、 三乙胺 、 sodium nitrite 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 66.0h， 生成 4-Methoxy-7-piperazin-1-yl-2-trifluoromethyl-[1,8]naphthyridine
  参考文献：
  名称：

  Synthesis of 1,8-naphthyridine derivatives: Potential antihypertensive agents — Part VII

  摘要：

  A series of 2-(carbethoxypiperazinyl)- and 2-piperazinyl-1,8-naphthyridine derivatives, variously substituted, have been synthesized and pharmacologically investigated for their antihypertensive activity. Some of them exhibited a significant and prolonged decrease of the mean arterial pressure (MAP) on spontaneously hypertensive rats. For this series of compounds, on the basis of the pharmacological results obtained, no structure-activity relationship can be deduced at this time. Moreover, the most active and representative compounds 11b, 12a and 16b were investigated by means of in vitro pharmacological functional studies and in vivo, as diuretic agents, to determine a possible mechanism of the antihypertensive activity, which is unknown for the moment. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80014-7
• 作为产物：
  描述：

  6-amino-2-(trifluoromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one 以 二苯醚 为溶剂， 反应 2.0h， 以90%的产率得到7-amino-4-hydroxy-2-trifluoromethyl-1,8-naphthyridine
  参考文献：
  名称：

  Synthesis of 1,8-naphthyridine derivatives: Potential antihypertensive agents — Part VII

  摘要：

  A series of 2-(carbethoxypiperazinyl)- and 2-piperazinyl-1,8-naphthyridine derivatives, variously substituted, have been synthesized and pharmacologically investigated for their antihypertensive activity. Some of them exhibited a significant and prolonged decrease of the mean arterial pressure (MAP) on spontaneously hypertensive rats. For this series of compounds, on the basis of the pharmacological results obtained, no structure-activity relationship can be deduced at this time. Moreover, the most active and representative compounds 11b, 12a and 16b were investigated by means of in vitro pharmacological functional studies and in vivo, as diuretic agents, to determine a possible mechanism of the antihypertensive activity, which is unknown for the moment. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80014-7

文献信息

• Structure-guided design, synthesis and biological evaluation of novel DNA ligase inhibitors with in vitro and in vivo anti-staphylococcal activity
  作者：Jean-Philippe Surivet、Roland Lange、Christian Hubschwerlen、Wolfgang Keck、Jean-Luc Specklin、Daniel Ritz、Daniel Bur、Hans Locher、Peter Seiler、Daniel Stefan Strasser、Lars Prade、Christopher Kohl、Christine Schmitt、Gaëlle Chapoux、Eser Ilhan、Nadia Ekambaram、Alcibiade Athanasiou、Andreja Knezevic、Daniela Sabato、Alain Chambovey、Mika Gaertner、Michel Enderlin、Maria Boehme、Virginie Sippel、Pierre Wyss

  DOI：10.1016/j.bmcl.2012.08.094

  日期：2012.11

  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.
• Synthesis of 1,8-naphthyridine derivatives: Potential antihypertensive agents — Part VII
  作者：Pier Luigi Ferrarini、Claudio Mori、Muwaffag Badawneh、Vincenzo Calderone、Lorella Calzolari、Tiziana Loffredo、Enrica Martinotti、Giuseppe Saccomanni

  DOI：10.1016/s0223-5234(98)80014-7

  日期：1998.6

  A series of 2-(carbethoxypiperazinyl)- and 2-piperazinyl-1,8-naphthyridine derivatives, variously substituted, have been synthesized and pharmacologically investigated for their antihypertensive activity. Some of them exhibited a significant and prolonged decrease of the mean arterial pressure (MAP) on spontaneously hypertensive rats. For this series of compounds, on the basis of the pharmacological results obtained, no structure-activity relationship can be deduced at this time. Moreover, the most active and representative compounds 11b, 12a and 16b were investigated by means of in vitro pharmacological functional studies and in vivo, as diuretic agents, to determine a possible mechanism of the antihypertensive activity, which is unknown for the moment. (C) Elsevier, Paris.