2-(4′-dimethylaminophenyl)-6-imidazo[1,2-a]pyridine | 14954-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4′-dimethylaminophenyl)-6-imidazo[1,2-a]pyridine
• 英文别名: 4-(imidazo[1,2-a]pyridin-2-yl)-N,N-dimethylaniline；2-[4-(dimethylamino)phenyl]imidazo[1,2-a]pyridine；2-(4'-dimethylamino)phenylimidazo[1,2-a]pyridine；4-(indolizin-2-yl)-N,N-dimethylbenzeneamine；2-(4'-N,N-dimethylamino)phenylimidazo[1,2-a]pyridine；IMPY；4-imidazo[1,2-a]pyridin-2-yl-N,N-dimethylaniline
• CAS: 14954-72-4
• 化学式: C₁₅H₁₅N₃
• mdl: MFCD22495137
• 分子量: 237.304
• InChiKey: QOULJXYVKZMPDM-UHFFFAOYSA-N

物化性质

• 熔点：
  192-193 °C(Solv: ethanol (64-17-5))
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 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：

  2-(4′-dimethylaminophenyl)-6-imidazo[1,2-a]pyridine 在 碘 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以52%的产率得到[4-(3-Iodo-imidazo[1,2-a]pyridin-2-yl)-phenyl]-dimethyl-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-(咪唑并[1,2-a]吡啶-2-基)苯胺 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-(4′-dimethylaminophenyl)-6-imidazo[1,2-a]pyridine
  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

• Substituent Effects on Fluorescent Properties of Imidazo[1,2-<b><i>a</i></b>]pyridine-Based Compounds
  作者：Haruhiko Tomoda、Takafumi Hirano、Shojiro Saito、Toshiki Mutai、Koji Araki

  DOI：10.1246/bcsj.72.1327

  日期：1999.6

  In order to search for novel fluorescent organic compounds, 20 derivatives of imidazo[1,2-a]pyridine (1) were synthesized, and their fluorescent properties were studied. Though the parent compound 1 (λfl = 370.5 nm, Φ = 0.57 in ethanol) was in the liquid state at ambient temperature, 2-phenylimidazo[1,2-a]pyridine (5), 2-(2-naphthyl)imidazo[1,2-a]pyridine (16), 7-methylimidazo[1,2-a]pyridine (3), 7-methyl-2-phenylimidazo[1,2-a]pyridine (12), and 7-methyl-2-(2-naphthyl)imidazo[1,2-a]pyridine (17) were found to give thermally stable solid compounds (mp 55—190 °C) without much affecting the fluorescent properties of the parent compound (λfl = 374—381 nm, Φ = 0.50—0.78 in ethanol). Among the 4′-substituted 2-phenyl derivatives, it was found that the introduction of the strong electron-donating amino and dimethylamino groups (2-(4-aminophenyl)imidazo[1,2-a]pyridine (7) and 2-[4-(dimethylamino)phenyl]imidazo[1,2-a]pyridine (8), respectively) caused marked red shift of their fluorescence (λfl = 445 and 446 nm, respectively, in ethanol), thus providing the way for tuning the fluorescence color of the IP derivatives. The observed red shift of the fluorescence of 7 and 8 was ascribed to the contribution of the excited intramolecular charge transfer state.

  为了寻找新型荧光有机化合物，合成了20种咪唑并[1,2-a]吡啶(1)的衍生物，并研究了它们的荧光性质。尽管母体化合物1在室温下为液态(λfl = 370.5 nm，Φ = 0.57，在乙醇中)，但2-苯基咪唑并[1,2-a]吡啶(5)、2-(2-萘基)咪唑并[1,2-a]吡啶(16)、7-甲基咪唑并[1,2-a]吡啶(3)、7-甲基-2-苯基咪唑并[1,2-a]吡啶(12)和7-甲基-2-(2-萘基)咪唑并[1,2-a]吡啶(17)被发现能形成热稳定的固态化合物(熔点55-190°C)，且对母体化合物的荧光性质影响不大(λfl = 374-381 nm，Φ = 0.50-0.78，在乙醇中)。在4'-取代的2-苯基衍生物中，发现引入强电子供体的氨基和二甲氨基(分别为2-(4-氨基苯基)咪唑并[1,2-a]吡啶(7)和2-[4-(二甲氨基)苯基]咪唑并[1,2-a]吡啶(8))会导致它们的荧光显著红移(λfl = 445和446 nm，在乙醇中)，从而提供了调节IP衍生物荧光颜色的途径。7和8荧光的红移归因于激发态分子内电荷转移态的贡献。
• Heterogeneously copper-catalyzed oxidative synthesis of imidazo[1,2-a]pyridines using 2-aminopyridines and ketones under ligand- and additive-free conditions
  作者：Xu Meng、Yanmin Wang、Chaoying Yu、Peiqing Zhao

  DOI：10.1039/c4ra03299c

  日期：——

  and mild heterogeneously CuCl2/nano-TiO2-catalyzed aerobic synthesis of imidazo[1,2-a]pyridines from 2-aminopyridines and ketones has been developed using air as the oxidant in the absence of any ligands and additives. This strategy was compatible with a large range of substrates, including unactivated aryl ketones and unsaturated ketones and went through the C–H bond functionalization mechanism instead

  利用空气作为氧化剂，在不存在任何配体和添加剂的情况下，开发了一种高效，温和的，异质性的CuCl 2 /纳米TiO 2催化的由2-氨基吡啶和酮类咪唑并[1,2- a ]吡啶的好氧合成方法。这个策略是具有大范围的底物相容的，包括未活化的芳基酮和不饱和酮，并通过C-H键的官能机构去的，而不是我- -assisted Ortoleva景反应以提供相应的咪唑并[1,2一以较低的催化剂负载量（0.8摩尔％）获得高产率的对吡啶。而且，该非均相催化剂可以成功地用于克规模的合成中并且可以多次重复使用而不会显着降低催化活性。
• Substituted imidazo[1,2-A] pyridine derivatives
  申请人：——

  公开号：US20020188128A1

  公开（公告）日：2002-12-12

  The present invention is a series of novel compounds of formula I and a method of treatment or prevention of a mGluR5 receptor mediated disease by administering an therapeutically effective amount of a compound formula 1 wherein R 1 and R 2 are selected from hydrogen, (C 1-6 )-alkyl, halogen, hydroxy, (C 1-6 )-alkoxy and A is defined the description, or a pharmaceutically acceptable salt thereof.

  本发明涉及一系列新颖的化合物，化学式为I，并通过给予有效治疗剂量的化合物化学式1来治疗或预防mGluR5受体介导的疾病的方法，其中R1和R2从氢、(C1-6)-烷基、卤素、羟基、(C1-6)-烷氧基中选择，A在描述中有定义，或其药用盐。
• Metal-Free Mediated C-3 Methylsulfanylation of Imidazo[1,2-a]-pyridines with Dimethyl Sulfoxide as a Methylsulfanylating Agent
  作者：Zhengkai Chen、Gangjian Cao、Fengjin Zhang、Hongli Li、Jianfeng Xu、Maozhong Miao、Hongjun Ren

  DOI：10.1055/s-0036-1588419

  日期：2017.9

  A simple approach is described for the regioselective C-3 methylsulfanylation of imidazo[1,2-a]pyridines through diiodine-­mediated, acetone-promoted, C–S bond construction with dimethyl sulfoxide as both the source of the methylsulfanyl moiety and the solvent. Preliminary mechanistic investigations indicated that three different reaction mechanisms might be involved in the transformation.

  一种简单的方法被描述用于通过二碘化物介导，丙酮促进，二甲基亚砜作为甲硫基单元来源和溶剂的C-3甲基硫酰化咪唑[1,2-a]吡啶的区域选择性反应。初步的机理研究表明，在反应转化中可能涉及三种不同的反应机制。
• Substituted imidazo [1,2-a] pyridine derivatives
  申请人：——

  公开号：US20030212096A1

  公开（公告）日：2003-11-13

  The present invention is a series of novel compounds of formula I and a method of treatment or prevention of a mGluR5 receptor mediated disease by administering an therapeutically effective amount of a compound formula 1 wherein R 1 and R 2 are selected from hydrogen, (C 1-6 )-alkyl, halogen, hydroxy, (C 1-6 )-alkoxy and A is defined the description, or a pharmaceutically acceptable salt thereof.

  本发明涉及一系列新型化合物I的方法，以及通过给予化合物公式1的治疗有效量或预防mGluR5受体介导的疾病的方法，其中R1和R2选择自氢，(C1-6)-烷基，卤素，羟基，(C1-6)-烷氧基和A在说明中定义，或其药学上可接受的盐。