4-[2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyridine | 425379-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-[2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyridine
• 英文别名: 4-(2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine；4-[2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine
• CAS: 425379-15-3
• 化学式: C₁₇H₁₉BFNO₂
• 分子量: 299.153
• InChiKey: RPVKFOWUQNUEHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol 、 4-[2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyridine 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 生成 2-[3-(4-Fluoro-3-pyridin-4-yl-phenyl)-imidazo[1,2-a]pyrimidin-7-yl]-propan-2-ol
  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 、 氢溴酸 、 potassium acetate 、 tin(ll) chloride 、 copper(I) bromide 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 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]-pyridine
  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

• Imidazo-pyrimidine derivatives as ligands for gaba receptors
  申请人：——

  公开号：US20020193385A1

  公开（公告）日：2002-12-19

  A class of 3-phenylimidazo[1,2-&agr;]pyrimidine 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, and further substituted on the phenyl ring by alkyl, trifluoromethyl, alkoxy or one or two halogen atoms, especially fluoro, are 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, and 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3-苯基咪唑[1,2-&agr;]嘧啶衍生物，苯环的间位被取代，取代基可以是直接连接或通过氧原子或-NH-键桥接的取代芳基或杂环芳基，苯环上进一步被取代为烷基，三氟甲基，烷氧基或一个或两个卤素原子，特别是氟，是GABAA受体的选择性配体，特别是对其中的&agr;2和/或&agr;3和/或&agr;5亚基具有良好的亲和力，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，惊厥和认知障碍具有益处。
• 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.