5'-amino-4, 2'-difluorobiphenyl-2-carbonitrile | 425378-82-1

• 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: 5'-amino-4, 2'-difluorobiphenyl-2-carbonitrile
• 英文别名: 2-(5-amino-2-fluorophenyl)-5-fluorobenzonitrile
• CAS: 425378-82-1
• 化学式: C₁₃H₈F₂N₂
• 分子量: 230.217
• InChiKey: HFCLWYJKVXCCGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 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：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5'-amino-4, 2'-difluorobiphenyl-2-carbonitrile 在 氢溴酸 、 copper(I) bromide 、 sodium nitrite 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 5'-bromo-2',4-difluorobiphenyl-2-carbonitrile
  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
• 作为产物：
  描述：

  4,2'-difluoro-5'-nitrobiphenyl-2-carbonitrile 在 二氧化铂 氢气 、 二氯甲烷 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 1.0h， 以to afford 5′-amino-4,2′-difluorobiphenyl-2-carbonitrile as a straw-coloured solid (23 g, 100%)的产率得到5'-amino-4, 2'-difluorobiphenyl-2-carbonitrile
  参考文献：
  名称：

  Imidazo-triazine derivatives as ligands for GABA receptors

  摘要：

  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。

  公开号：

  US06936608B2

文献信息

• [EN] IMIDAZO-PYRIDINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS<br/>[FR] DERIVES D'IMIDAZO-PYRIDINE UTILISES EN TANT QUE LIGANDS POUR LES RECEPTEURS GABA
  申请人：MERCK SHARP & DOHME

  公开号：WO2003099816A1

  公开（公告）日：2003-12-04

  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 -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-苯基咪唑并[1,2-a]吡啶衍生物，通过苯环的间位被一个可选择取代的芳基或杂环芳基团，或者通过一个吡咯烷基团取代，该吡咯烷基团直接连接或通过氧原子或-NH-或-OCH2-键连接，作为GABAA受体的选择性配体，特别是对其α2和/或α3和/或α5亚基具有高亲和力，因此在治疗和/或预防中枢神经系统的不良状况，包括焦虑、惊厥和认知障碍方面具有益处。
• 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。
• [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。
• [EN] IMIDAZO-PYRIMIDINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS<br/>[FR] DERIVES D'IMIDAZO-PYRIMIDINE UTILISES COMME LIGANDS POUR LES RECEPTEURS GABA
  申请人：MERCK SHARP & DOHME

  公开号：WO2002074772A1

  公开（公告）日：2002-09-26

  A class of 3-phenylimidazo[1,2-a]pyrimidine derivatives, substituted at the meta position of the phenyl ring by a directly attached, optionally halo- and/or cyano-substituted aryl or heteroaryl group, and further substituted on the phenyl ring by one or two fluorine atoms, are selective ligands for GABAA receptors, in particular having good affinity for the α2 and/or α3 and/or α5 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-a]嘧啶衍生物，取代苯环的间位，直接连接一个可选择的卤素和/或氰基取代的芳基或杂环基团，并在苯环上进一步取代一个或两个氟原子，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。