2-(4-bromophenyl)imidazo[1,2-a]pyridine-6-carbonitrile | 731822-49-4

• 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-bromophenyl)imidazo[1,2-a]pyridine-6-carbonitrile
• CAS: 731822-49-4
• 化学式: C₁₄H₈BrN₃
• 分子量: 298.142
• InChiKey: NYSJHIIOGCWKSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-bromophenyl)imidazo[1,2-a]pyridine-6-carbonitrile 在 四(三苯基膦)钯 、 tetraphosphorus decasulfide 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 6.0h， 生成 6-(4-methyl-4,5-dihydroimidazol-2-yl)-2-{4-[6-(4-methyl-4,5-dihydroimidazol-2-yl)indol-3-yl]phenyl}imidazo[1,2-a]pyridine acetic acid salt
  参考文献：
  名称：

  [EN] ANTIMICROBIAL COMPOUNDS
  [FR] COMPOSÉS ANTIMICROBIENS

  摘要：

  这项发明提供了抗微生物有机化合物及其组合物，可杀灭或抑制一种或多种微生物病原体的细胞生长。

  公开号：

  WO2013040527A1
• 作为产物：
  描述：

  2-氨基-5-氰基吡啶 、 2,4'-二溴苯乙酮 以 乙醇 为溶剂， 反应 24.0h， 以67%的产率得到2-(4-bromophenyl)imidazo[1,2-a]pyridine-6-carbonitrile
  参考文献：
  名称：

  新颖的咪唑并[1,2-a]吡啶和5,6,7,8-四氢咪唑并[1,2-a]吡啶作为抗原生动物剂。

  摘要：

  合成2- [5-（4-A基苯基）-呋喃-2-基] -5,6,7,8-四氢咪唑并[1,2-a]吡啶-6-邻甲氧box乙酸盐（7）通过双-O-乙酰氧基ami肟将2- [5-（4-氰基苯基）-呋喃-2-基]-咪唑并[1,2-a]吡啶-6-腈（4a），然后在冰醋酸中氢化。以四个步骤获得化合物4a，首先先用N-溴代琥珀酰亚胺连续两次溴化2-乙酰基呋喃，然后再用溴连续溴化以中等产率形成α-溴-2-乙酰基-5-溴呋喃（2）。6-氨基-烟腈与2之间缩合反应的产物（3a）与4-氰基苯基硼酸进行Suzuki偶联，以高收率得到4a。从4a获得2- [5-（4-ami基苯基）-呋喃-2-基]-咪唑并[1,2-a]吡啶-6-羧am的乙酸盐（8a），通过双-O-乙酰氧基酰胺肟，然后在乙醇/乙酸乙酯的混合物中氢化。N-甲氧基-2-（5- [4-（N-甲氧基ami基）-苯基]-呋喃-2-基）-咪唑并[1,2-a]吡啶-6

  DOI：

  10.1021/jm0400092

文献信息

• Novel dicationic imidazo[1,2-a]pyridines and 5,6,7,8,-tetrahydro-imidazo[1,2,-a]pyridines as antiprotozoal agents
  申请人：Boykin W. David

  公开号：US20050282853A1

  公开（公告）日：2005-12-22

  A method for treating a microbial infection, including an infection from a protozoan pathogen, such as Trypanosoma brucei rhodesiense and Plasmodium falciparum , in a subject in need thereof by administering to the subject an effective amount of a dicationic imidazopyridine compound or a dicationic tetrahydro-imidazopyridine compound. Processes for synthesizing dicationic imidazopyridines and dicationic tetrahydro-imidazopyridines and the novel dicationic imidazopyridine and dicationic tetrahydro-imidazopyridine compounds themselves.

  一种治疗微生物感染的方法，包括治疗来自原虫病原体（如Trypanosoma brucei rhodesiense和Plasmodium falciparum）的感染，通过向需要的对象施用有效量的二阳离子咪唑吡啶化合物或二阳离子四氢咪唑吡啶化合物。合成二阳离子咪唑吡啶和二阳离子四氢咪唑吡啶的方法，以及新型的二阳离子咪唑吡啶和二阳离子四氢咪唑吡啶化合物本身。
• Synthesis and antibacterial evaluation of new, unsymmetrical triaryl bisamidine compounds
  作者：Son T. Nguyen、John D. Williams、Michelle M. Butler、Xiaoyuan Ding、Debra M. Mills、Tommy F. Tashjian、Rekha G. Panchal、Susan K. Weir、Chaeho Moon、Hwa-Ok Kim、Jeremiah A. Marsden、Norton P. Peet、Terry L. Bowlin

  DOI：10.1016/j.bmcl.2014.05.094

  日期：2014.8

  is a benzimidazole, imidazopyridine, benzofuran, benzothiophene, pyrimidine or benzene ring. When the [HetAr/Ar] unit is a 5,6-bicyclic heterocycle, it is oriented such that the 5-membered ring portion is connected to the [linker] unit and the 6-membered ring portion is connected to the [Am] unit. Among the 34 compounds in this series, compounds with benzofuran as the [HetAr/Ar] unit showed the highest

  在此，我们描述了一种新型不对称三芳基双脒化合物系列[Am]-[吲哚]-[连接基]-[HetAr/Ar]-[Am]的合成和抗菌评价，其中[Am]是脒或氨基[连接体]为苯环、噻吩环或吡啶环，[HetAr/Ar]为苯并咪唑、咪唑并吡啶、苯并呋喃、苯并噻吩、嘧啶或苯环。[HetAr/Ar]单元为5,6-二环杂环时，其取向为5元环部分与[连接基]单元连接，6元环部分与[Am]连接。单元。在该系列的 34 种化合物中，以苯并呋喃为 [HetAr/Ar] 单元的化合物显示出最高的效力。在三芳基核心中引入氟原子或甲基会产生更有效的类似物。双脒对细菌更具活性，而单脒对哺乳动物细胞更活性（如低 CC 50值所示）。重要的是，我们发现化合物P12a (MBX 1887) 具有相对较窄的抗菌谱和非常高的 CC 50值。化合物P12a已扩大规模，目前正在接受进一步的治疗应用评估。
• Effect of cyano substituent on the functional properties of blue emitting Imidazo[1,2-a]pyridine derivatives
  作者：Anupriya、K.R. Justin Thomas、Mangey Ram Nagar、Jwo-Huei Jou

  DOI：10.1016/j.dyepig.2022.110658

  日期：2022.10

  the photo-induced intramolecular charge transfer between donors and cyano-imidazo[1,2-a]pyridine acceptor. Addition of the cyano group on imidazopyridine restrained the formation of aggregates in the solid-state and stabilized the lowest unoccupied molecular orbital. Among the all, doped devices constructed with 3 wt% of triphenylamine containing dye revealed excellent performance in the series with a

  有机发光体中的高荧光效率和平衡的电荷传输是 OLED 应用的理想特性。通常，表现出显着分子内电荷转移的供体-受体化合物表现出低荧光量子产率。在这里，我们报道了含有 CN 取代的 2-苯基咪唑并[1,2- a ] 吡啶受体单元的 DA 荧光团，它们表现出良好的荧光特性。给体（三苯胺/咔唑）和氰基取代基的位置分别互换，得到一系列异构体。所有荧光团均表现出较高的荧光量子产率（Ф f ≥  0.70）和优异的热稳定性（T d10 ≥ 390 °C）。在C2苯环的对位包含三苯胺单元的染料表现出红移的发射最大值，在系列中具有较大的斯托克斯位移。此外，由于供体和氰基咪唑并[1,2- a ]吡啶受体之间的光诱导分子内电荷转移，所有异构体都表现出激发态溶剂化变色。在咪唑并吡啶上添加氰基抑制了固态聚集体的形成并稳定了最低的未占分子轨道。其中，使用 3 wt% 三苯胺染料构建的掺杂器件在系列中表现出优异的性能，最大
• Synthesis and antifungal evaluation of head-to-head and head-to-tail bisamidine compounds
  作者：Son T. Nguyen、Steven M. Kwasny、Xiaoyuan Ding、John D. Williams、Norton P. Peet、Terry L. Bowlin、Timothy J. Opperman

  DOI：10.1016/j.bmc.2015.07.006

  日期：2015.9

  Herein, we describe the antifungal evaluation of 43 bisamidine compounds, of which 26 are new, having the scaffold [Am]-[HetAr]-[linker]-[HetAr]-[Am], in which [Am] is a cyclic or acyclic amidine group, [linker] is a benzene, pyridine, pyrimidine, pyrazine ring, or an aliphatic chain of two to four carbon, and [HetAr] is a 5,6-bicyclic heterocycle such as indole, benzimidazole, imidazopyridine, benzofuran, or benzothiophene. In the head-to-head series the two [HetAr] units are oriented such that the 5-membered rings are connected through the linker, and in the head-to-tail series, one of the [HetAr] systems is connected through the 6-membered ring; additionally, in some of the head-to-tail compounds, the [linker] is omitted. Many of these compounds exhibited significant antifungal activity against Candida albicans, Candida krusei, Candida glabrata, Candida parapsilosis, and Cryptococcus neoformans (MIC <= 4 mu g/ml). The most potent compounds, for example, P10, P19 and P34, are comparable in antifungal activities to amphotericin B (MIC 0.125 mu g/ml). They exhibited rapid fungicidal activity (>3 log(10) decrease in cfu/ml in 4 h) at concentrations equivalent to 4x the MIC in time kill experiments. The bisamidines strongly inhibited DNA, RNA and cell wall biosynthesis in C. albicans in macromolecular synthesis assays. However, the half-maximal inhibitory concentration for DNA synthesis was approximately 30-fold lower than those for RNA and cell wall biosynthesis. Fluorescence microscopy of intact cells of C. albicans treated with a bisamidine exhibited enhanced fluorescence in the presence of DNA, demonstrating that the bisamidine was localized to the nucleus. The results of this study show that bisamidines are potent antifungal agents with rapid fungicidal activity, which is likely to be the result of their DNA-binding activity. Although it was difficult to obtain a broad-spectrum antifungal compound with low cytotoxicity, some of the compounds (e.g., P9, P14 and P43) exhibited favorable CC50 values against HeLa cells and maintained considerable antifungal activity. (C) 2015 Elsevier Ltd. All rights reserved.
• NOVEL DICATIONIC IMIDAZO 1,2-a PYRIDINES AND 5,6,7,8-TE TRAHYDRO-IMIDAZO 1,2a PYRIDINES AS ANTIPROTOZOAL AGENTS
  申请人：THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP1745045A2

  公开（公告）日：2007-01-24