6,2'-difluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile | 425379-22-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6,2'-difluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile
• 英文别名: 6,2'-Difluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrile；3-fluoro-2-[2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzonitrile
• CAS: 425379-22-2
• 化学式: C₁₉H₁₈BF₂NO₂
• 分子量: 341.165
• InChiKey: JGEHOZIBWQGIAS-UHFFFAOYSA-N

物化性质

• 沸点：
  456.4±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,2'-difluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile 在 四(三苯基膦)钯 、 氢溴酸 、 caesium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 6,2'-Difluoro-5'-(8-oxo-7,8-dihydro-imidazo[1,2-a]pyrazin-3-yl)-biphenyl-2-carbonitrile
  参考文献：
  名称：

  Imidazo[1,2-a]pyrazin-8-ones, imidazo[1,2-d][1,2,4]triazin-8-ones and imidazo[2,1-f][1,2,4]triazin-8-ones as α2/α3 subtype selective GABAA agonists for the treatment of anxiety

  摘要：

  Imidazo[1,2-a]pyrazin-8-ones, imidazo[1, 2-d] [ 1, 2,4]triazin-8 -ones and imidazo[2,1-f][1,2,4]triazin-8-ones are high affinity GABA(A) agonists. Compound 16d has good oral bioavailability in rat, functional selectivity for the GABA(A) alpha 2 and alpha 3-subtypes and is anxiolytic in a conditioned animal model of anxiety with minimal sedation observed at full BZ binding site occupancy. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.027
• 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 6,2'-difluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile
  参考文献：
  名称：

  Imidazo[1,2-a]pyrazin-8-ones, imidazo[1,2-d][1,2,4]triazin-8-ones and imidazo[2,1-f][1,2,4]triazin-8-ones as α2/α3 subtype selective GABAA agonists for the treatment of anxiety

  摘要：

  Imidazo[1,2-a]pyrazin-8-ones, imidazo[1, 2-d] [ 1, 2,4]triazin-8 -ones and imidazo[2,1-f][1,2,4]triazin-8-ones are high affinity GABA(A) agonists. Compound 16d has good oral bioavailability in rat, functional selectivity for the GABA(A) alpha 2 and alpha 3-subtypes and is anxiolytic in a conditioned animal model of anxiety with minimal sedation observed at full BZ binding site occupancy. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.027

文献信息

• Imidazo-triazine derivatives as ligands for GABA receptors
  申请人：——

  公开号：US20030055060A1

  公开（公告）日：2003-03-20

  A class of 7-phenylimidazo[1,2-b][1,2,4]triazine derivatives, substituted at the meta position of the phenyl ring by a (cyano)(fluoro)phenyl moiety, being selective ligands for GABA A receptors, in particular having good affinity for the &agr;2 and/or &agr;3 subunit thereof, are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety and convulsions.

  一类7-苯基咪唑[1,2-b][1,2,4]三嗪衍生物，通过在苯环的间位上取代（氰基）（氟基）苯基基团，作为GABA受体的选择性配体，特别是对其α2和/或α3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，包括焦虑和惊厥，具有益处。
• 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-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。
• Phenylpyridazine derivatives as ligands for gaba receptors
  申请人：Blackaby Wesley

  公开号：US20060235021A1

  公开（公告）日：2006-10-19

  A class of 4-phenylpyridazine derivatives of Formula (I), being selective ligands for GABA A receptors, in particular having high 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4-苯基吡嗪衍生物(I式)，是选择性的GABAA受体配体，特别是具有高亲和力的α2和/或α3和/或α5亚单位，因此对于治疗和/或预防中枢神经系统的不良病症，包括焦虑，惊厥和认知障碍具有益处。
• Imidazo[1,2<i>-a</i>]pyrimidines as Functionally Selective and Orally Bioavailable GABA_Aα2/α3 Binding Site Agonists for the Treatment of Anxiety Disorders
  作者：Simon C. Goodacre、Leslie J. Street、David J. Hallett、James M. Crawforth、Sarah Kelly、Andrew P. Owens、Wesley P. Blackaby、Richard T. Lewis、Joanna Stanley、Alison J. Smith、Pushpinder Ferris、Bindi Sohal、Susan M. Cook、Andrew Pike、Nicola Brown、Keith A. Wafford、George Marshall、José L. Castro、John R. Atack

  DOI：10.1021/jm051065l

  日期：2006.1.1

  A series of high-affinity GABA(A) agonists with good oral bioavailability in rat and dog and functional selectivity for or the GABA(A)alpha 2 and -alpha 3 subtypes is reported. The 7-trifluoroinethylimidazopyrimidine 14g and the 7-propan-2-olimidazopyrimidine 14k are anxiolytic in both conditioned and unconditioned animal models of anxiety with minimal sedation observed at full BZ binding site occupancy.