N-[4-[tert-butyl(diphenyl)silyl]oxy-2-fluorophenyl]-7-fluoro-3-oxo-2,5-dihydro-1H-pyrido[1,2-a]benzimidazole-4-carboxamide | 205700-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: N-[4-[tert-butyl(diphenyl)silyl]oxy-2-fluorophenyl]-7-fluoro-3-oxo-2,5-dihydro-1H-pyrido[1,2-a]benzimidazole-4-carboxamide
• CAS: 205700-48-7
• 化学式: C₃₄H₃₁F₂N₃O₃Si
• 分子量: 595.721
• InChiKey: AGRFBJBMCTZVKS-UHFFFAOYSA-N

物化性质

• 沸点：
  645.5±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  43.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  70.67
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-[4-[tert-butyl(diphenyl)silyl]oxy-2-fluorophenyl]-7-fluoro-3-oxo-2,5-dihydro-1H-pyrido[1,2-a]benzimidazole-4-carboxamide 在 15-冠醚-5 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-Fluoro-1,2-dihydro-5-ethoxymethyl-3-oxo-N-(2-fluoro-4-hydroxyphenyl)pyrido[1,2-a]benzimidazole-4-carboxamide
  参考文献：
  名称：

  Potential Anxiolytic Agents. Part 4: Novel Orally-Active N5-Substituted Pyrido[1,2-a]benzimidazoles with High GABA-A Receptor Affinity

  摘要：

  A series of pyrido[1,2-a]benzimidazoles (PBIs) with substitution on the N-5-nitrogen has been synthesized and found to possess high affinity for the benzodiazepine (BZD) site on the GABA-A receptor. The compounds evaluated include those bearing a heteroalkyl group and heterocyclic rings. The most promising of these compounds is ethoxymethyl analogue 24, which has an IC50 of 0.1 nM for the BZD site on the GABA-A receptor and has been advanced to human clinical trials. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00463-8
• 作为产物：
  描述：

  3-氟-4-硝基苯酚 在 palladium on activated charcoal 咪唑 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 140.0 ℃ 、379.21 kPa 条件下， 生成 N-[4-[tert-butyl(diphenyl)silyl]oxy-2-fluorophenyl]-7-fluoro-3-oxo-2,5-dihydro-1H-pyrido[1,2-a]benzimidazole-4-carboxamide
  参考文献：
  名称：

  Potential Anxiolytic Agents. Part 4: Novel Orally-Active N5-Substituted Pyrido[1,2-a]benzimidazoles with High GABA-A Receptor Affinity

  摘要：

  A series of pyrido[1,2-a]benzimidazoles (PBIs) with substitution on the N-5-nitrogen has been synthesized and found to possess high affinity for the benzodiazepine (BZD) site on the GABA-A receptor. The compounds evaluated include those bearing a heteroalkyl group and heterocyclic rings. The most promising of these compounds is ethoxymethyl analogue 24, which has an IC50 of 0.1 nM for the BZD site on the GABA-A receptor and has been advanced to human clinical trials. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00463-8

文献信息

• 5-HETEROATOM-CONTAINING ALKYL SUBSTITUTED-3-OXO-PYRIDO(1,2-a) BENZIMIDAZOLE-4-CARBOXAMIDE DERIVATIVES USEFUL IN TREATING CENTRAL NERVOUS SYSTEM DISORDERS
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：EP0935598B1

  公开（公告）日：2003-12-10