7-Fluoro-1,2-dihydro-5-ethoxymethyl-3-oxo-N-(2-fluoro-4-hydroxyphenyl)pyrido[1,2-a]benzimidazole-4-carboxamide | 205701-16-2

• 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: 7-Fluoro-1,2-dihydro-5-ethoxymethyl-3-oxo-N-(2-fluoro-4-hydroxyphenyl)pyrido[1,2-a]benzimidazole-4-carboxamide
• 英文别名: 5-(ethoxymethyl)-7-fluoro-N-(2-fluoro-4-hydroxyphenyl)-3-oxo-1,2-dihydropyrido[1,2-a]benzimidazole-4-carboxamide
• CAS: 205701-16-2
• 化学式: C₂₁H₁₉F₂N₃O₄
• 分子量: 415.396
• InChiKey: KRISMRBLGCMOEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  82.1
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  氯甲酸甲酯 、 7-Fluoro-1,2-dihydro-5-ethoxymethyl-3-oxo-N-(2-fluoro-4-hydroxyphenyl)pyrido[1,2-a]benzimidazole-4-carboxamide 在 吡啶 作用下， 以 氯仿 为溶剂， 生成 [4-[[5-(Ethoxymethyl)-7-fluoro-3-oxo-1,2-dihydropyrido[1,2-a]benzimidazole-4-carbonyl]amino]-3-fluorophenyl] methyl carbonate
  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：

  4-{[tert-Butyl(diphenyl)silyl]oxy}-2-fluoroaniline 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 、 xylene 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

文献信息

• Pyrido[1,2-a]benzimidazole derivatives useful in treating central nervous system disorders
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：EP1420018A1

  公开（公告）日：2004-05-19

  A compound of general formula (1) is disclosed as useful in treating disorders of the central nervous system. Pharmaceutical compositions and methods of treatment are also disclosed.

  通式（1）化合物被公开用于治疗中枢神经系统疾病。 还公开了药物组合物和治疗方法。
• 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
• US5817668A
  申请人：——

  公开号：US5817668A

  公开（公告）日：1998-10-06
• Potential Anxiolytic Agents. Part 4: Novel Orally-Active N5-Substituted Pyrido[1,2-a]benzimidazoles with High GABA-A Receptor Affinity
  作者：Alfonzo D Jordan、Anil H Vaidya、Daniel I Rosenthal、Barry Dubinsky、Cheryl P Kordik、Pauline J Sanfilippo、Wu-Nan Wu、Allen B Reitz

  DOI：10.1016/s0960-894x(02)00463-8

  日期：2002.9

  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.