Methyl-[4-(6-methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-amine | 497848-14-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Methyl-[4-(6-methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-amine
• 英文别名: N-methyl-4-(6-methylimidazo[1,2-a]pyridin-2-yl)aniline
• CAS: 497848-14-3
• 化学式: C₁₅H₁₅N₃
• 分子量: 237.304
• InChiKey: BZCLHXUEJWOHES-UHFFFAOYSA-N

物化性质

• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 Methyl-[4-(6-methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-amine 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 Dimethyl-[4-(6-methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-amine
  参考文献：
  名称：

  Structure−Activity Relationship of Imidazo[1,2-a]pyridines as Ligands for Detecting β-Amyloid Plaques in the Brain

  摘要：

  A series of novel beta-amyloid (Abeta) aggregate-specific ligands, 2-(4'-dimethylaminophenyl)-6-iodoimidazo[1,2-alpha]pyridine, (IMPY), and its related derivatives were prepared. An in vitro binding study with preformed Abeta aggregates showed that 16(IMPY) and its bromo derivative competed with binding of 2-(4'-dimethylaminophenyl)-6-iodobenzothiazole, [I-125]7(TZDM), a known ligand for Abeta aggregates, with high binding affinities (K-i = 15 and 10 nM, respectively). In vitro autoradiography of brain sections of a transgenic mouse (Tg2576) with [I-125]16(IMPY) displayed high selective binding to amyloid-like structures, comparable to that observed by staining with thioflavin-S visualized under fluorescence. In vivo biodistribution after an intravenous injection of [I-125]16(IMPY) in normal mice showed a high initial brain uptake and fast washout, indicating a low background activity associated with this iodinated ligand. Taken together, the data suggests that [I-123]16(IMPY) may be useful for imaging Abeta aggregates in patients with Alzheimer's disease.

  DOI：

  10.1021/jm020351j
• 作为产物：
  描述：

  4-{6-methylimidazo[1,2-a]pyridin-2-yl}aniline 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 Methyl-[4-(6-methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-amine
  参考文献：
  名称：

  Structure−Activity Relationship of Imidazo[1,2-a]pyridines as Ligands for Detecting β-Amyloid Plaques in the Brain

  摘要：

  A series of novel beta-amyloid (Abeta) aggregate-specific ligands, 2-(4'-dimethylaminophenyl)-6-iodoimidazo[1,2-alpha]pyridine, (IMPY), and its related derivatives were prepared. An in vitro binding study with preformed Abeta aggregates showed that 16(IMPY) and its bromo derivative competed with binding of 2-(4'-dimethylaminophenyl)-6-iodobenzothiazole, [I-125]7(TZDM), a known ligand for Abeta aggregates, with high binding affinities (K-i = 15 and 10 nM, respectively). In vitro autoradiography of brain sections of a transgenic mouse (Tg2576) with [I-125]16(IMPY) displayed high selective binding to amyloid-like structures, comparable to that observed by staining with thioflavin-S visualized under fluorescence. In vivo biodistribution after an intravenous injection of [I-125]16(IMPY) in normal mice showed a high initial brain uptake and fast washout, indicating a low background activity associated with this iodinated ligand. Taken together, the data suggests that [I-123]16(IMPY) may be useful for imaging Abeta aggregates in patients with Alzheimer's disease.

  DOI：

  10.1021/jm020351j

文献信息

• USRE44338E1
  申请人：——

  公开号：USRE44338E1

  公开（公告）日：2013-07-02
• USRE44354E1
  申请人：——

  公开号：USRE44354E1

  公开（公告）日：2013-07-09
• Structure−Activity Relationship of Imidazo[1,2-<i>a</i>]pyridines as Ligands for Detecting β-Amyloid Plaques in the Brain
  作者：Zhi-Ping Zhuang、Mei-Ping Kung、Alan Wilson、Chi-Wan Lee、Karl Plössl、Catherine Hou、David M. Holtzman、Hank F. Kung

  DOI：10.1021/jm020351j

  日期：2003.1.1

  A series of novel beta-amyloid (Abeta) aggregate-specific ligands, 2-(4'-dimethylaminophenyl)-6-iodoimidazo[1,2-alpha]pyridine, (IMPY), and its related derivatives were prepared. An in vitro binding study with preformed Abeta aggregates showed that 16(IMPY) and its bromo derivative competed with binding of 2-(4'-dimethylaminophenyl)-6-iodobenzothiazole, [I-125]7(TZDM), a known ligand for Abeta aggregates, with high binding affinities (K-i = 15 and 10 nM, respectively). In vitro autoradiography of brain sections of a transgenic mouse (Tg2576) with [I-125]16(IMPY) displayed high selective binding to amyloid-like structures, comparable to that observed by staining with thioflavin-S visualized under fluorescence. In vivo biodistribution after an intravenous injection of [I-125]16(IMPY) in normal mice showed a high initial brain uptake and fast washout, indicating a low background activity associated with this iodinated ligand. Taken together, the data suggests that [I-123]16(IMPY) may be useful for imaging Abeta aggregates in patients with Alzheimer's disease.