3-bromo-5-propyl-1,6-naphthyridin-2(1H)-one | 169228-05-1

• 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: 3-bromo-5-propyl-1,6-naphthyridin-2(1H)-one
• 英文别名: 3-bromo-5-propyl-1H-1,6-naphthyridin-2-one
• CAS: 169228-05-1
• 化学式: C₁₁H₁₁BrN₂O
• 分子量: 267.125
• InChiKey: GPXRPKBRWCJYGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-5-propyl-1,6-naphthyridin-2(1H)-one 在 N-甲基吡咯烷酮 、 氨 、 三氯氧磷 作用下， 反应 39.0h， 生成 8-propylthiazolo<4,5-b><1,6>naphthyridine-2(3H)-thione
  参考文献：
  名称：

  Novel and Potent Adenosine 3',5'-Cyclic Phosphate Phosphodiesterase III Inhibitors: Thiazolo[4,5-b][1,6]naphthyridin-2-ones

  摘要：

  The transformation of 3-bromo-1,6-naphthyridin-2(1H)-ones 8 to thiazolo[4,5-b][1,6]naphthyridin-2(1H)-ones 12 resulted in a 2-9-fold increase in cAMP phosphodiesterase (PDE) III inhibitory potency. Unlike the secondary binding sites on the cAMP PDE III isozyme which interact with the methyl group of milrinone (2) and CI-930 (4), the site which interacts with the 5-substituents of 1,6-naphthyridin-2(1H)-ones and the 8-substituents of thiazolo[4,5-b][1,6]-naphthyridin-2(1H)-ones 12 is able to accommodate a diverse group of substituents which have different steric and electronic requirements.

  DOI：

  10.1021/jm00014a007
• 作为产物：
  描述：

  5-(n-butanoyl)-6-methyl-2(1H)-pyridinone 在 乙酸铵 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 18.0h， 生成 3-bromo-5-propyl-1,6-naphthyridin-2(1H)-one
  参考文献：
  名称：

  Novel and Potent Adenosine 3',5'-Cyclic Phosphate Phosphodiesterase III Inhibitors: Thiazolo[4,5-b][1,6]naphthyridin-2-ones

  摘要：

  The transformation of 3-bromo-1,6-naphthyridin-2(1H)-ones 8 to thiazolo[4,5-b][1,6]naphthyridin-2(1H)-ones 12 resulted in a 2-9-fold increase in cAMP phosphodiesterase (PDE) III inhibitory potency. Unlike the secondary binding sites on the cAMP PDE III isozyme which interact with the methyl group of milrinone (2) and CI-930 (4), the site which interacts with the 5-substituents of 1,6-naphthyridin-2(1H)-ones and the 8-substituents of thiazolo[4,5-b][1,6]-naphthyridin-2(1H)-ones 12 is able to accommodate a diverse group of substituents which have different steric and electronic requirements.

  DOI：

  10.1021/jm00014a007

文献信息

• Novel and Potent Adenosine 3',5'-Cyclic Phosphate Phosphodiesterase III Inhibitors: Thiazolo[4,5-b][1,6]naphthyridin-2-ones
  作者：Baldev Singh、Edward R. Bacon、George Y. Lesher、Shaughnessy Robinson、Patrick O. Pennock、Donald C. Bode、Edward D. Pagani、Ross G. Bentley、Mary J. Connell、Linda T. Hamel、Paul J. Silver

  DOI：10.1021/jm00014a007

  日期：1995.7

  The transformation of 3-bromo-1,6-naphthyridin-2(1H)-ones 8 to thiazolo[4,5-b][1,6]naphthyridin-2(1H)-ones 12 resulted in a 2-9-fold increase in cAMP phosphodiesterase (PDE) III inhibitory potency. Unlike the secondary binding sites on the cAMP PDE III isozyme which interact with the methyl group of milrinone (2) and CI-930 (4), the site which interacts with the 5-substituents of 1,6-naphthyridin-2(1H)-ones and the 8-substituents of thiazolo[4,5-b][1,6]-naphthyridin-2(1H)-ones 12 is able to accommodate a diverse group of substituents which have different steric and electronic requirements.