4-hydroxy-3-(pyrrolidin-1-ylcarbonyl)-1,8-naphthyridin-2(1H)-one | 1060775-08-7

• 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: 4-hydroxy-3-(pyrrolidin-1-ylcarbonyl)-1,8-naphthyridin-2(1H)-one
• CAS: 1060775-08-7
• 化学式: C₁₃H₁₃N₃O₃
• 分子量: 259.265
• InChiKey: UOZWKTSDACZZNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  86.29
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-(pyrrolidin-1-ylcarbonyl)-1,8-naphthyridin-2(1H)-one 在 三氯氧磷 作用下， 反应 1.0h， 以56%的产率得到(2,4-dichloro-1,8-naphthyridin-3-yl)(1-pyrrolidinyl)methanone
  参考文献：
  名称：

  1,8-Naphthyridines VII. New substituted 5-amino[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides and their isosteric analogues, exhibiting notable anti-inflammatory and/or analgesic activities, but no acute gastrolesivity

  摘要：

  The [1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamide derivatives 5-amino (2) or 5-alkoxy (3) substituted and the 5-amino[1,2,4] triazolo[4,3-a]quinoline-4-carboxamide derivatives (4), designed to obtain new effective analgesic and/or anti-inflammatory agents were synthesized. Ten compounds 2 and 4 showed an interesting analgesic activity: the most potent ones are 2j (36% inhibition, P < 0.05) and 4b (77% inhibition, P < 0.01) at 6.25 and 25 mg kg(-1) doses, respectively. Compounds 2i-I and 4c showed notable anti-inflammatory properties: the most potent ones are 2i (68% inhibition, P < 0.01) and 21 (42% inhibition, P < 0.05) at 12.5 and 6.25 mg kg(-1) doses, respectively. The replacement in compounds 2 of the N-substituted 5-amino substituents with similar alkoxy groups usually afforded less active compounds 3. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.10.010
• 作为产物：
  描述：

  四氢吡咯 、 methyl 1,2-dihydro-4-hydroxy-2-oxo-1,8-naphthyridine-3-carboxylate 以 乙醇 为溶剂， 反应 16.0h， 以93%的产率得到4-hydroxy-3-(pyrrolidin-1-ylcarbonyl)-1,8-naphthyridin-2(1H)-one
  参考文献：
  名称：

  1,8-Naphthyridines VII. New substituted 5-amino[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides and their isosteric analogues, exhibiting notable anti-inflammatory and/or analgesic activities, but no acute gastrolesivity

  摘要：

  The [1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamide derivatives 5-amino (2) or 5-alkoxy (3) substituted and the 5-amino[1,2,4] triazolo[4,3-a]quinoline-4-carboxamide derivatives (4), designed to obtain new effective analgesic and/or anti-inflammatory agents were synthesized. Ten compounds 2 and 4 showed an interesting analgesic activity: the most potent ones are 2j (36% inhibition, P < 0.05) and 4b (77% inhibition, P < 0.01) at 6.25 and 25 mg kg(-1) doses, respectively. Compounds 2i-I and 4c showed notable anti-inflammatory properties: the most potent ones are 2i (68% inhibition, P < 0.01) and 21 (42% inhibition, P < 0.05) at 12.5 and 6.25 mg kg(-1) doses, respectively. The replacement in compounds 2 of the N-substituted 5-amino substituents with similar alkoxy groups usually afforded less active compounds 3. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.10.010