4-(3H-imidazo[4,5-b]pyridin-2-yl)benzonitrile | 89454-67-1

• 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-(3H-imidazo[4,5-b]pyridin-2-yl)benzonitrile
• 英文别名: 4-(1H-imidazo[4,5-b]pyridin-2-yl)benzonitrile
• CAS: 89454-67-1
• 化学式: C₁₃H₈N₄
• mdl: MFCD16239418
• 分子量: 220.233
• InChiKey: SBEHOQVAOUNCSL-UHFFFAOYSA-N

物化性质

• 沸点：
  429.2±47.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3H-imidazo[4,5-b]pyridin-2-yl)benzonitrile 在 盐酸羟胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以56%的产率得到N-hydroxy-4-(3H-imidazo[4,5-b]pyridin-2-yl)benzenecarboximidamide
  参考文献：
  名称：

  Synthesis and potent cytotoxicity of some novel imidazopyridine derivatives against MCF-7 human breast adenocarcinoma cell line

  摘要：

  A series of novel 2-phenyl-3H-imidazo[4,5-b]pyridines and 2-phenyl-3H-imidazo[4,5-c]pyridines and their precursors were synthesized. Their in vitro cytotoxicity against MCF-7 human breast adenocarcinoma cell line has been investigated, and some of the tested compounds have shown high cytotoxic activity against MCF-7 cells. N-Hydroxy-4-(3H-imidazo[4,5-b]pyridin-2-yl)benzenecarboximidamide was the most active compound with IC50 equal to 0.082 mu M, which is an activity almost as high as that of a commonly used anticancer drugs docetaxel and imatinib mesylate.

  DOI：

  10.1007/s10593-015-1765-7
• 作为产物：
  描述：

  N-benzyl-3-nitropyridin-2-amine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 110.0 ℃ 、275.8 kPa 条件下， 反应 4.0h， 生成 4-(3H-imidazo[4,5-b]pyridin-2-yl)benzonitrile
  参考文献：
  名称：

  Synthesis and potent cytotoxicity of some novel imidazopyridine derivatives against MCF-7 human breast adenocarcinoma cell line

  摘要：

  A series of novel 2-phenyl-3H-imidazo[4,5-b]pyridines and 2-phenyl-3H-imidazo[4,5-c]pyridines and their precursors were synthesized. Their in vitro cytotoxicity against MCF-7 human breast adenocarcinoma cell line has been investigated, and some of the tested compounds have shown high cytotoxic activity against MCF-7 cells. N-Hydroxy-4-(3H-imidazo[4,5-b]pyridin-2-yl)benzenecarboximidamide was the most active compound with IC50 equal to 0.082 mu M, which is an activity almost as high as that of a commonly used anticancer drugs docetaxel and imatinib mesylate.

  DOI：

  10.1007/s10593-015-1765-7

文献信息

• Synthesis and antiviral activity of new phenylimidazopyridines and N-benzylidenequinolinamines derived by molecular simplification of phenylimidazo[4,5-g]quinolines
  作者：Roberta Loddo、Irene Briguglio、Paola Corona、Sandra Piras、Mario Loriga、Giuseppe Paglietti、Antonio Carta、Giuseppina Sanna、Gabriele Giliberti、Cristina Ibba、Pamela Farci、Paolo La Colla

  DOI：10.1016/j.ejmech.2014.07.011

  日期：2014.9

  assays for cytotoxicity and antiviral activity against representatives of two DNA virus families as wells as against representatives of RNA virus families containing single-stranded, either positive-sense (ssRNA+) or negative-sense (ssRNA−), and double-stranded genomes (dsRNA). Some imidazo[4,5-b]pyridines emerged as new derivatives endowed with antiviral activity against Vaccinia Virus (VV) at concentrations

  继续进行有关一系列新的角和线性偶氮双环和三环衍生物的抗病毒活性的研究计划，现在我们简化并修饰了4-氯-2-（4-硝基苯基）-3 H-咪唑[4，通过消除中心环或咪唑环的打开，先前产生活性最高的衍生物的5- g ]喹啉1分别获得各种咪唑并吡啶和N-亚苄基喹啉胺。 标题化合物中的细胞毒性和抗病毒活性对两个DNA病毒科的代表，孔中作为对含有单链，无论是正链（单链RNA的RNA病毒科的代表基于细胞的测定中测试+）或负义单链RNA（-）和双链基因组（dsRNA）。一些咪唑并[4,5- b ]吡啶以新衍生物的形式出现，在2至16μM的浓度范围内具有抗痘苗病毒（VV）的抗病毒活性。特别是，化合物2b的功效比用作参考药物的西多福韦强约10倍。同样，咪唑并[4,5- c ]吡啶和N-亚苄基喹啉胺衍生物在1.2至28μM的浓度范围内具有抗牛病毒性腹泻病毒（BVDV）的活性。所有上述化合物1，图3a和3f中显示出EC
• Biological Activity of Amidino-Substituted Imidazo [4,5-b]pyridines
  作者：Ida Boček Pavlinac、Katarina Zlatić、Leentje Persoons、Dirk Daelemans、Mihajlo Banjanac、Vedrana Radovanović、Kristina Butković、Marijeta Kralj、Marijana Hranjec

  DOI：10.3390/molecules28010034

  日期：——

  amidino-substituted imidazo[4,5-b]pyridines were synthesized using standard methods of organic synthesis, and their biological activity was evaluated. Biological evaluation included in vitro assessment of antiproliferative effects on a diverse selection of human cancer cell lines, antibacterial activity against chosen Gram-positive and Gram-negative bacterial strains, and antiviral activity on a broad panel of DNA

  使用有机合成的标准方法合成了一系列氰基和脒基取代的咪唑并 [4,5-b] 吡啶，并评估了它们的生物活性。生物学评估包括体外评估对多种人类癌细胞系的抗增殖作用、对选定的革兰氏阳性和革兰氏阴性细菌菌株的抗菌活性，以及​​对广泛的 DNA 和 RNA 病毒的抗病毒活性。对于含有未取代的脒基的化合物 10 和含有 2-咪唑啉基脒基的化合物 14，观察到最显着的抗增殖活性；两者在亚微摩尔抑制浓度范围内均显示出对结肠癌的选择性和强活性（IC50 分别为 0.4 和 0.7 μM）。所有测试的化合物都缺乏抗菌活性，化合物 14 除外，它对大肠杆菌显示出中等活性（MIC 32 μM）。含有未取代苯环的溴代衍生物 7 (EC50 21 μM) 和对氰基取代衍生物 17 (EC50 58 μM) 对呼吸道合胞病毒 (RSV) 表现出选择性但中等的活性。
• Hit generation and exploration: Imidazo[4,5-b]pyridine derivatives as inhibitors of Aurora kinases
  作者：Vassilios Bavetsias、Chongbo Sun、Nathalie Bouloc、Jóhannes Reynisson、Paul Workman、Spiros Linardopoulos、Edward McDonald

  DOI：10.1016/j.bmcl.2007.09.076

  日期：2007.12

  A hit generation and exploration approach led to the discovery of 31 (2-(4-(6-chloro-2-(4-(dimethylamino) phenyl)-3H-imidazo[4,5-b] pyridin-7-yl) piperazin-1-yl)-N-(thiazol-2-yl) acetamide), a potent, novel inhibitor of Aurora-A, Aurora-B and Aurora-C kinases with IC50 values of 0.042, 0.198 and 0.227 mu M, respectively. Compound 31 inhibits cell proliferation and has good microsomal stability. (c) 2007 Elsevier Ltd. All rights reserved.