2-氰基-2-氟联苯-3-基硼酸 | 425378-90-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氰基-2-氟联苯-3-基硼酸
• 英文名称: 2'-cyano-2-fluorobiphenyl-3-boronic acid
• 英文别名: 2'-Cyano-2-fluorobiphenyl-3-ylboronic acid；[3-(2-cyanophenyl)-2-fluorophenyl]boronic acid
• CAS: 425378-90-1
• 化学式: C₁₃H₉BFNO₂
• 分子量: 241.029
• InChiKey: PODKTOWRSBFDPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-溴-7-(三氟甲基)咪唑并[1,2-a]嘧啶 、 2-氰基-2-氟联苯-3-基硼酸 以to give 2′-fluoro-3′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile as an off-white solid (70 mg, 18%)的产率得到2-Fluoro-3-(7-trifluoromethylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile
  参考文献：
  名称：

  Imidazo-pyrimidine derivatives as ligands for gaba receptors

  摘要：

  一类3-苯基咪唑并[1,2-α]嘧啶衍生物，取代苯环的间位，由一个可选取代的芳基或杂环芳基团直接或通过氧原子或—NH—键桥接，苯环上进一步取代了烷基，三氟甲基，烷氧基或一个或两个卤素原子，特别是氟原子，是GABAA受体的选择性配体，特别是对α2和/或α3和/或α5亚单位具有良好的亲和力，因此有助于治疗和/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。

  公开号：

  US06900215B2
• 作为产物：
  描述：

  2'-fluoro-[1,1'-biphenyl]-2-carbonitrile 在 2,2,6,6-四甲基哌啶 、 正丁基锂 、 硼酸三甲酯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以67%的产率得到2-氰基-2-氟联苯-3-基硼酸
  参考文献：
  名称：

  Imidazo[1,2-a]pyrimidines as Functionally Selective and Orally Bioavailable GABA_Aα2/α3 Binding Site Agonists for the Treatment of Anxiety Disorders

  摘要：

  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.

  DOI：

  10.1021/jm051065l

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-pyridine derivatives as ligands for gaba receptors
  申请人：Goodacre Charles Simon

  公开号：US20050165048A1

  公开（公告）日：2005-07-28

  A class of 8-fluoro-3-phenylimidazo[1,2-a]pyridine derivatives, substituted at the meta position of the phenyl ring by an optionally substituted aryl or heteroaryl group, or by a pyrrolidinonyl group, which is directly attached or bridged by an oxygen atom or by a —NH— or —OCH 2 — linkage, 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8-氟-3-苯基咪唑[1,2-a]吡啶衍生物，取代苯环的间位的芳基或杂环基或吡咯烷基，可以是可选的取代基，或是直接通过氧原子或- NH-或-OCH2-连接桥接，是GABAA受体的选择性配体，特别是具有对其α2和/或α3和/或α5亚基高亲和力，因此有益于治疗和/或预防中枢神经系统的不良症状，包括焦虑，抽搐和认知障碍。
• 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-pyridine derivatives as ligands for GABA receptors
  申请人：Merck Sharp & Dohme Limited

  公开号：US07279580B2

  公开（公告）日：2007-10-09

  A class of 8-fluoro-3-phenylimidazo[1,2-α]pyridine derivatives, substituted at the meta position of the phenyl ring by an optionally substituted aryl or heteroaryl group, or by a pyrrolidinonyl group, which is directly attached or bridged by an oxygen atom or by a —NH— or —OCH2— linkage, being selective ligands for GABAA 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8-氟-3-苯基咪唑[1,2-α]吡啶衍生物，苯环的间位被一个可选择取代的芳基或杂环基团或一个吡咯烷基取代，该基团通过氧原子或者-NH-或-OCH2-链直接连接或桥接，是GABAA受体的选择性配体，特别是对其中的α2和/或α3和/或α5亚单位具有高亲和力。因此，这些化合物有益于治疗和/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。
• Imidazo-triazine derivatives as ligands for GABA receptors
  申请人：Bettati Michela

  公开号：US06936608B2

  公开（公告）日：2005-08-30

  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 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，其苯环的间位取代为直接连接或通过氧原子或—NH—键桥接的可选取代芳基或杂环芳基基团，是GABAA受体的选择性配体，特别是具有良好的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。