4-(2-Fluoro-5-nitro-phenyl)-pyrimidine-5-carbonitrile | 425379-59-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(2-Fluoro-5-nitro-phenyl)-pyrimidine-5-carbonitrile
• 英文别名: 4-(2-Fluoro-5-nitrophenyl)pyrimidine-5-carbonitrile
• CAS: 425379-59-5
• 化学式: C₁₁H₅FN₄O₂
• 分子量: 244.185
• InChiKey: DWQBEXIVYXPAIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(2-Fluoro-5-nitro-phenyl)-pyrimidine-5-carbonitrile 在 氢溴酸 、 tin(ll) chloride 、 copper(I) bromide 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-[2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Imidazo[1,2-b][1,2,4]triazines as α2/α3 subtype selective GABAA agonists for the treatment of anxiety

  摘要：

  Imidazo[1,2-a]pyrimidines and imidazo[1,2-b][1,2,4]triazines are ligands for the benzodiazepine binding site of GABA(A) receptors that are functionally selective for the alpha 2/alpha 3 subtypes over the alpha 1 subtype. SAR studies to optimise this functional selectivity, pharmacokinetic and behavioural data are described. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.044
• 作为产物：
  描述：

  3-溴-4-氟硝基苯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium fluoride 、 tris(dibenzylideneacetone)dipalladium (0) 、 三叔丁基膦 、 potassium acetate 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 4-(2-Fluoro-5-nitro-phenyl)-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Imidazo[1,2-b][1,2,4]triazines as α2/α3 subtype selective GABAA agonists for the treatment of anxiety

  摘要：

  Imidazo[1,2-a]pyrimidines and imidazo[1,2-b][1,2,4]triazines are ligands for the benzodiazepine binding site of GABA(A) receptors that are functionally selective for the alpha 2/alpha 3 subtypes over the alpha 1 subtype. SAR studies to optimise this functional selectivity, pharmacokinetic and behavioural data are described. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.044

文献信息

• [EN] IMIDAZO-TRIAZINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS<br/>[FR] DERIVES D'IMIDAZO-TRIAZINE COMME LIGANDS DE RECEPTEURS GABA
  申请人：MERCK SHARP & DOHME

  公开号：WO2002038568A1

  公开（公告）日：2002-05-16

  A class of 7-phenylimidazo [1,2-b][1,2,4]triazine derivatives, substituted at the meta position of the phenyl ring by an optionally substituted aryl or heteroaryl group which is directly attached or bridged by an oxygen atom or a -NH- linkage, being selective ligands for GABAA receptors, in particular having good affinity for the α2 and/or α3 and/or α5 subunit thereof, are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.

  一类7-苯基咪唑[1,2-b][1,2,4]三嗪衍生物，取代苯环的间位上，由一个可选择取代的芳基或杂环芳基基团直接连接或通过氧原子或-NH-键桥接，是选择性的GABAA受体配体，特别是对其α2和/或α3和/或α5亚单位具有良好的亲和力，因此对于治疗和/或预防中枢神经系统的不良症状，包括焦虑、惊厥和认知障碍是有益的。
• Imidazo-triazine derivatives as ligands for gaba receptors
  申请人：——

  公开号：US20040023964A1

  公开（公告）日：2004-02-05

  A class of 7-phenylimidazo[1,2-b][1,2,4]triazine derivatives, substituted at the meta position of the phenyl ring by an optionally substituted aryl or heteroaryl group which is directly attached or bridged by an oxygen atom or a —NH— linkage, being selective ligands for GABA A receptors, in particular having good affinity for the &agr;2 and/or &agr;3 and/or &agr;5 subunit thereof, are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.

  一类7-苯基咪唑[1,2-b][1,2,4]三嗪衍生物，其苯环的间位被一个可选择取代的芳基或杂环芳基基团取代，该基团直接连接或由氧原子或-NH-键桥接，是选择性的GABAA受体配体，特别是具有良好的对α2和/或α3和/或α5亚单位的亲和力，因此对于治疗和/或预防中枢神经系统的不良症状，包括焦虑，惊厥和认知障碍具有益处。
• IMIDAZO-TRIAZINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP1343788A1

  公开（公告）日：2003-09-17
• US6936608B2
  申请人：——

  公开号：US6936608B2

  公开（公告）日：2005-08-30
• Imidazo[1,2-b][1,2,4]triazines as α2/α3 subtype selective GABAA agonists for the treatment of anxiety
  作者：Andrew S.R. Jennings、Richard T. Lewis、Michael G.N. Russell、David J. Hallett、Leslie J. Street、José L. Castro、John R. Atack、Susan M. Cook、Rachael Lincoln、Joanna Stanley、Alison J. Smith、David S. Reynolds、Bindi Sohal、Andrew Pike、George R. Marshall、Keith A. Wafford、Wayne F.A. Sheppard、Spencer J. Tye

  DOI：10.1016/j.bmcl.2005.12.044

  日期：2006.3

  Imidazo[1,2-a]pyrimidines and imidazo[1,2-b][1,2,4]triazines are ligands for the benzodiazepine binding site of GABA(A) receptors that are functionally selective for the alpha 2/alpha 3 subtypes over the alpha 1 subtype. SAR studies to optimise this functional selectivity, pharmacokinetic and behavioural data are described. (C) 2006 Elsevier Ltd. All rights reserved.