(E)-tert-butyl 3-(3-(4-fluorobenzyl)-6-oxo-7-((2-(trimethylsilyl)ethoxy)methoxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)acrylate | 1293387-95-7

• 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: (E)-tert-butyl 3-(3-(4-fluorobenzyl)-6-oxo-7-((2-(trimethylsilyl)ethoxy)methoxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)acrylate
• 英文别名: tert-butyl (E)-3-[3-[(4-fluorophenyl)methyl]-6-oxo-7-(2-trimethylsilylethoxymethoxy)-8,9-dihydropyrrolo[2,3-c][1,7]naphthyridin-1-yl]prop-2-enoate
• CAS: 1293387-95-7
• 化学式: C₃₀H₃₈FN₃O₅Si
• 分子量: 567.733
• InChiKey: LUTAIFMFOLKITN-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  82.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-tert-butyl 3-(3-(4-fluorobenzyl)-6-oxo-7-((2-(trimethylsilyl)ethoxy)methoxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)acrylate 在 氢气 、 palladium(II) hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以87%的产率得到tert-butyl 3-(3-(4-fluorobenzyl)-6-oxo-7-((2-(trimethylsilyl)ethoxy)methoxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoate
  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 N-碘代丁二酰亚胺 、 palladium diacetate 、 sodium cyanoborohydride 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 (E)-tert-butyl 3-(3-(4-fluorobenzyl)-6-oxo-7-((2-(trimethylsilyl)ethoxy)methoxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)acrylate
  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