4-(6-bromo-imidazo[1,2-a]pyridin-2-yl)-N,N-dimethylbenzenamine | 474012-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(6-bromo-imidazo[1,2-a]pyridin-2-yl)-N,N-dimethylbenzenamine
• 英文别名: 6-Bromo-2-(4'-Dimethylamino-)Phenyl-Imidazo [1,2-a] pyridine；[4-(6-Bromo-imidazo[1,2-a]pyridin-2-yl)-phenyl]-dimethyl-amine；4-(6-bromoimidazo[1,2-a]pyridin-2-yl)-N,N-dimethylaniline
• CAS: 474012-67-4
• 化学式: C₁₅H₁₄BrN₃
• 分子量: 316.2
• InChiKey: VAHGJFIWCIDKJM-UHFFFAOYSA-N

物化性质

• 熔点：
  233-235 °C
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 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：
  20.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(6-bromo-imidazo[1,2-a]pyridin-2-yl)-N,N-dimethylbenzenamine 在 钯 三乙胺 、 碘 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 生成 4-(6-iodo-imidazo[1,2-a]pyridin-2-yl)-N,N-dimethylbenzenamine
  参考文献：
  名称：

  Zhuang, Z. P.; Kung, M.-P.; Hou, C., Journal of labelled compounds and radiopharmaceuticals, 2001, vol. 44, p. S29 - S32

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-5-溴吡啶 、 2-溴-1-(4-二甲基氨基苯基)乙酮 以 乙醇 为溶剂， 生成 4-(6-bromo-imidazo[1,2-a]pyridin-2-yl)-N,N-dimethylbenzenamine
  参考文献：
  名称：

  Amyloid plaque aggregation inhibitors and diagnostic imaging agents

  摘要：

  本发明涉及成像淀粉样沉积物的方法，以及标记化合物和制备标记化合物的方法，用于成像淀粉样沉积物。本发明还涉及化合物和制备化合物的方法，用于抑制淀粉样蛋白聚集形成淀粉样沉积物，并提供一种将治疗剂递送到淀粉样沉积物的方法。

  公开号：

  US20030059369A1

文献信息

• Compounds and methods useful for rescuing cells from beta-amyloid toxicity and treatment of Alzheimer's disease
  申请人：Jin Lee-Way

  公开号：US20070254889A1

  公开（公告）日：2007-11-01

  The present invention is directed to pharmaceutical compositions comprising one or more compounds of Formulae I, II, III, IV, V, VI, VII, VIII, IX and X, or pharmaceutically acceptable salts thereof and excipients. The present invention provides a method of inhibiting β-amyloid plaque aggregation, the method comprising introducing into a mammal an aggregation-inhibiting amount of a compound of Formula I, II, III, IV, V, VI, VII, VIII, IX or X or a pharmaceutically acceptable salt, ester, amide or prodrug thereof. By inhibiting amyloid aggregation, this method is capable of rescuing cells that otherwise would be susceptible or further damaged by amyloidosis.

  本发明涉及一种制药组合物，包括式I、II、III、IV、V、VI、VII、VIII、IX和X中的一个或多个化合物，或其药学上可接受的盐和辅料。本发明提供了一种抑制β-淀粉样斑块聚集的方法，该方法包括向哺乳动物中引入式I、II、III、IV、V、VI、VII、VIII、IX或X中的一种化合物或其药学上可接受的盐、酯、酰胺或前药的抑制聚集量。通过抑制淀粉样聚集，该方法能够挽救那些本来易受淀粉样蛋白病损伤的细胞。
• BETA-AMYLOID PET IMAGING AGENTS
  申请人：Cai Lisheng

  公开号：US20110008255A1

  公开（公告）日：2011-01-13

  Novel derivatives of imidazopyridinylbenzeneamines and novel derivatives of benzothiazolylbenzeneamines are disclosed that offer improved behavior when used as imaging agents for positron emission tomography of beta-amyloids. Also disclosed is a palladium-catalyzed reaction scheme under microwave conditions for aryl thioethers in general that provides a high ratio of substitution relative to reduction and can be used for the imidazopyridinylbenzeneamine derivatives as well as other compounds of related structure.

  本发明揭示了新型咪唑吡啶基苯胺衍生物和新型苯并噻唑基苯胺衍生物，用作正电子发射断层扫描成像剂时表现出改进的行为。还揭示了一种钯催化反应方案，在微波条件下对芳基硫醚进行反应，相对于还原提供更高的取代比，并可用于咪唑吡啶基苯胺衍生物以及其他相关结构的化合物。
• Beta-Amyloid Pet Imaging Agents
  申请人：The Government Of The United States, As Represented by The Secretary Of Health And Human Services

  公开号：EP2808020A1

  公开（公告）日：2014-12-03

  A compound having the formula wherein: R11 is a member selected from the group consisting of C1-C6 alkyl, aryl- or halo- substituted C1-C6 alkyl, hydroxyl-substituted C1-C6 alkyl, and carbamoyl C1-C6 alkyl; R12 is a member selected from the group consisting of H, C1-C6 alkyl, halo-substituted C1-C6 alkyl, halo, and C1-C6 alkylthio, and R13 is a member selected from the group consisting of H and C1-C3 alkyl, or R12 and R13 are joined to form a thio-C1-C3 alkylene or alkylene linkage, and R14 is a member selected from the group consisting of H and C1-C6 alkyl, and X is CH or N.

  一种化合物，其化学式为 其中 R11 是选自由 C1-C6 烷基、芳基或卤代 C1-C6 烷基、羟基取代的 C1-C6 烷基和卤代 C1-C6 烷基组成的组。 取代的 C1-C6 烷基、羟基取代的 C1-C6 烷基和 氨基甲酰基 C1-C6 烷基； R12 是选自 H、C1-C6 烷基、卤代 C1-C6 烷基、卤代 C1-C6 烷基、卤代 C1-C6 烷基和氨基甲酰基 C1-C6 烷基的成员 C1-C6烷基、卤代和 C1-C6 烷硫基，R13 是选自 H 和 C1-C3 烷基组成的组的成员，或 R12 和 R13 连接形成硫代-C1-C3 亚烷基或亚烷基连接，R14 是选自 H 和 C1-C6 烷基组成的组的成员，X 是 CH 或 N。
• WO2007/124345
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.