1-[[(2-fluorophenyl)methoxy]methyl]-3-(4-fluorobenzyl)-3,7,8,9-tetrahydro-7-{[2-(trimethylsilyl)ethoxy]methoxy}-6H-pyrrolo[2,3-c]-[1,7]naphthyridin-6-one | 1293388-16-5

• 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: 1-[[(2-fluorophenyl)methoxy]methyl]-3-(4-fluorobenzyl)-3,7,8,9-tetrahydro-7-{[2-(trimethylsilyl)ethoxy]methoxy}-6H-pyrrolo[2,3-c]-[1,7]naphthyridin-6-one
• 英文别名: 1-[(2-Fluorophenyl)methoxymethyl]-3-[(4-fluorophenyl)methyl]-7-(2-trimethylsilylethoxymethoxy)-8,9-dihydropyrrolo[2,3-c][1,7]naphthyridin-6-one
• CAS: 1293388-16-5
• 化学式: C₃₁H₃₅F₂N₃O₄Si
• 分子量: 579.719
• InChiKey: XKJJKIPFCAVOBL-UHFFFAOYSA-N

物化性质

• 沸点：
  714.8±60.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  65.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[[(2-fluorophenyl)methoxy]methyl]-3-(4-fluorobenzyl)-3,7,8,9-tetrahydro-7-{[2-(trimethylsilyl)ethoxy]methoxy}-6H-pyrrolo[2,3-c]-[1,7]naphthyridin-6-one 在 盐酸 、 水 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 15.0h， 以50%的产率得到1-[ [ (2-fluorophenyl)methoxy]methyl]-3-(4-fluorobenzyl)-3,7,8,9-tetrahydro-7-hydroxy-6H-pyrrolo[2,3-c][1,7]naphthyridin-6-one hydrochloride
  参考文献：
  名称：

  Design and Synthesis of Novel N-Hydroxy-Dihydronaphthyridinones as Potent and Orally Bioavailable HIV-1 Integrase Inhibitors

  摘要：

  HIV-1 integrase (IN) is one of three enzymes encoded by the HIV genome and is essential for viral replication, and HIV-1 IN inhibitors have emerged as a new promising class of therapeutics. Recently, we reported the synthesis of orally bioavailable azaindole hydroxamic acids that were potent inhibitors of the HIV-1 IN enzyme. Here we disclose the design and synthesis of novel tricyclic N-hydroxy-dihydronaphthyridinones as potent, orally bioavailable HIV-1 integrase inhibitors displaying excellent ligand and lipophilic efficiencies.

  DOI：

  10.1021/jm200208d
• 作为产物：
  描述：

  O-((2-trimethylsilylethoxy)methyl)hydroxylamine 在 sodium cyanoborohydride 、 对甲苯磺酸 、 溶剂黄146 、 N,N-二异丙基乙胺 、 氯甲酸苯酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 104.0h， 生成 1-[[(2-fluorophenyl)methoxy]methyl]-3-(4-fluorobenzyl)-3,7,8,9-tetrahydro-7-{[2-(trimethylsilyl)ethoxy]methoxy}-6H-pyrrolo[2,3-c]-[1,7]naphthyridin-6-one
  参考文献：
  名称：

  Design and Synthesis of Novel N-Hydroxy-Dihydronaphthyridinones as Potent and Orally Bioavailable HIV-1 Integrase Inhibitors

  摘要：

  HIV-1 integrase (IN) is one of three enzymes encoded by the HIV genome and is essential for viral replication, and HIV-1 IN inhibitors have emerged as a new promising class of therapeutics. Recently, we reported the synthesis of orally bioavailable azaindole hydroxamic acids that were potent inhibitors of the HIV-1 IN enzyme. Here we disclose the design and synthesis of novel tricyclic N-hydroxy-dihydronaphthyridinones as potent, orally bioavailable HIV-1 integrase inhibitors displaying excellent ligand and lipophilic efficiencies.

  DOI：

  10.1021/jm200208d