3-(7-methylimidazo[1,2-a]pyridin-3-yl)phenol | 342613-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(7-methylimidazo[1,2-a]pyridin-3-yl)phenol
• CAS: 342613-57-4
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: MGMSARFNBIVJLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(7-methylimidazo[1,2-a]pyridin-3-yl)phenol 在 吡啶 、 1,1'-双(二苯基膦)二茂铁 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 7-methyl-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]imidazo[1,2-a]pyridine
  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：

  3-bromo-7-甲基-咪唑并[1,2-a]吡啶 在 四(三苯基膦)钯 、 氢溴酸 、 sodium carbonate 、 溶剂黄146 作用下， 以 乙二醇二甲醚 为溶剂， 反应 35.0h， 生成 3-(7-methylimidazo[1,2-a]pyridin-3-yl)phenol
  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-pyridine derivatives as ligands for gaba receptors
  申请人：——

  公开号：US20020188000A1

  公开（公告）日：2002-12-12

  A class of 3-phenylimidazo[1,2-a]pyridine 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, are selective ligands for GABA A receptors, in particular having high affinity for the &agr;2 and/or &agr;3 subunit thereof, and are accordingly of benefit in the treatment and/or prevention of disorders of the central nervous system, including anxiety and convulsions.

  一类3-苯基咪唑[1,2-a]吡啶衍生物，苯环的间位取代一个可选取代芳基或杂环芳基，该芳基或杂环芳基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亚基具有高亲和力，因此对于治疗和/或预防中枢神经系统疾病，包括焦虑和惊厥，具有益处。
• Imidazo-pyridine derivatives as ligands for GABA receptors
  申请人：Crawforth James Michael

  公开号：US06872731B2

  公开（公告）日：2005-03-29

  A class of 3-phenylimidazo[1,2-a]pyridine 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, are selective ligands for GABA A receptors, in particular having high affinity for the α2 and/or α3 subunit thereof, and are accordingly of benefit in the treatment and/or prevention of disorders of the central nervous system, including anxiety and convulsions.

  一类3-苯基咪唑[1,2-a]吡啶衍生物，苯环的间位被取代为可选取代芳基或杂环基团，该基团直接连接或通过氧原子或-NH-连接桥接，是GABAA受体的选择性配体，特别是对α2和/或α3亚单位具有高亲和力，因此对于治疗和/或预防中枢神经系统紊乱，包括焦虑和惊厥等方面具有益处。
• IMIDAZO-PYRIDINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP1235827A2

  公开（公告）日：2002-09-04
• [EN] IMIDAZO-PYRIDINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS<br/>[FR] DERIVES D'IMIDAZO-PYRIDINE UTILISES COMME LIGANDS POUR RECEPTEURS DE GABA
  申请人：MERCK SHARP & DOHME

  公开号：WO2001038326A2

  公开（公告）日：2001-05-31

  A class of 3-phenylimidazo[1,2-a]pyridine 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, are selective ligands for GABAA receptors, in particular having high affinity for the α2 and/or α3 subunit thereof, and are accordingly of benefit in the treatment and/or prevention of disorders of the central nervous system, including anxiety and convulsions.