3-(4-fluorobenzyl)-1-iodo-7-{[2-(trimethylsilyl)ethoxy]methoxy}-8,9-dihydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-6(7H)-one | 1161880-19-8

• 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-(4-fluorobenzyl)-1-iodo-7-{[2-(trimethylsilyl)ethoxy]methoxy}-8,9-dihydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-6(7H)-one
• 英文别名: 3-(4-fluorobenzyl)-1-iodo-7-{[2-(trimethylsilyl)ethoxy]methoxy}-3,7,8,9-tetrahydro-6H-pyrrolo[2,3-c]-1,7-naphthyridin-6-one；3-(4-fluorobenzyl)-1-iodo-7-{[2-(trimethylsilyl)ethoxy]methoxy}-3,7,8,9-tetrahydro-6H-pyrrolo[2,3-c][1,7]naphthyridin-6-one；3-[(4-fluorophenyl)methyl]-1-iodo-7-(2-trimethylsilylethoxymethoxy)-8,9-dihydropyrrolo[2,3-c][1,7]naphthyridin-6-one
• CAS: 1161880-19-8
• 化学式: C₂₃H₂₇FIN₃O₃Si
• 分子量: 567.474
• InChiKey: GETMPKROZYYLMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  56.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-fluorobenzyl)-1-iodo-7-{[2-(trimethylsilyl)ethoxy]methoxy}-8,9-dihydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-6(7H)-one 在 硫酸 、 氢气 、 palladium diacetate 、 palladium(II) hydroxide 、 三乙胺 、 异丙醇 、 三(邻甲基苯基)磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 40.0~80.0 ℃ 、101.33 kPa 条件下， 反应 32.0h， 生成
  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 、 sodium cyanoborohydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 63.0h， 生成 3-(4-fluorobenzyl)-1-iodo-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

文献信息

• INHIBITORS OF THE HIV INTEGRASE ENZYME
  申请人：Dress Ruprecht Klaus

  公开号：US20070099915A1

  公开（公告）日：2007-05-03

  The present invention is directed to compounds of formula (I), and pharmaceutically acceptable salts and solvates thereof, their synthesis, and their use as modulators or inhibitors of the human immunodeficiency virus (“HIV”) integrase enzyme.

  本发明涉及式（I）的化合物，以及其在药学上可接受的盐和溶剂化合物，它们的合成，以及它们作为人类免疫缺陷病毒（“HIV”）整合酶的调节剂或抑制剂的用途。