methyl 1-(4-fluorobenzyl)-4-(2-((2-(trimethylsilyl)ethoxy)methoxyimino)ethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate | 934621-51-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: methyl 1-(4-fluorobenzyl)-4-(2-((2-(trimethylsilyl)ethoxy)methoxyimino)ethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate
• 英文别名: Methyl 1-[(4-fluorophenyl)methyl]-4-[2-(2-trimethylsilylethoxymethoxyimino)ethyl]pyrrolo[2,3-c]pyridine-5-carboxylate
• CAS: 934621-51-9
• 化学式: C₂₄H₃₀FN₃O₄Si
• 分子量: 471.604
• InChiKey: COAVCDIOGOUCBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 1-(4-fluorobenzyl)-4-(2-((2-(trimethylsilyl)ethoxy)methoxyimino)ethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 反应 2.0h， 以84%的产率得到3-(4-fluorobenzyl)-7-((2-(trimethylsilyl)ethoxy)methoxy)-8,9-dihydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-6(7H)-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
• 作为产物：
  描述：

  methyl 1-(4-fluorobenzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 N-甲基二环己基胺 、 对甲苯磺酸 、 三乙胺 、 lithium chloride 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 61.0h， 生成 methyl 1-(4-fluorobenzyl)-4-(2-((2-(trimethylsilyl)ethoxy)methoxyimino)ethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate
  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