6-bromo-2-(4-methoxyphenyl)-1H-imidazo [4,5-b]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-bromo-2-(4-methoxyphenyl)-1H-imidazo [4,5-b]pyridine
• 英文别名: 6-Bromo-2-(4-methoxyphenyl)-3h-imidazo[4,5-b]pyridine；6-bromo-2-(4-methoxyphenyl)-1H-imidazo[4,5-b]pyridine
• 化学式: C₁₃H₁₀BrN₃O
• mdl: MFCD01052898
• 分子量: 304.146
• InChiKey: KXXNSRRQEABRTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-bromo-2-(4-methoxyphenyl)-1H-imidazo [4,5-b]pyridine 在 trisodium tris-(3-sulfonatophenyl)phosphine trihydrate 、 palladium diacetate 、 caesium carbonate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 水 、 二甲胺 、 乙腈 为溶剂， 反应 0.08h， 生成 4-[2-(4-methoxyphenyl)-1H-imidazo[4,5-b]pyridin-6-yl]-N-(2-methylpropyl)thiophene-2-carboxamide
  参考文献：
  名称：

  Discovery of 6-aryl-azabenzimidaoles that inhibit the TBK1/IKK-ε kinases

  摘要：

  The discovery and optimization of a series of 6-aryl-azabenzimidazole inhibitors of TBK1 and IKK-epsilon is described. Various internal azabenzimidazole leads and reported TBK1/IKK-epsilon inhibitors were docked into a TBK1 homology model. The resulting overlays inspired a focused screen of 6-substituted azabenzimidazoles against TBK1/IKK-epsilon. This screen resulted in initial hit compound 3. The TBK1/IKK-epsilon enzyme and cell potency of this compound was further improved using structure guided drug design. Systematic exploration of the C6 aryl group led to compound 19, a potent inhibitor of TBK1 with selectivity against cell cycle kinases CDK2 and Aurora B. Further elaboration and optimization gave compound 25, a single digit nM inhibitor of TBK1. These compounds may serve as in vitro probes to evaluate TBK1/IKK-epsilon as an oncology target. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.123
• 作为产物：
  描述：

  2,3-二氨基-5-溴吡啶 在 PPA 作用下， 以 吡啶 为溶剂， 反应 2.0h， 生成 6-bromo-2-(4-methoxyphenyl)-1H-imidazo [4,5-b]pyridine
  参考文献：
  名称：

  Dubey; Vinod Kumar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 10, p. 746 - 751

  摘要：

  DOI：

文献信息

• [EN] USE OF AND SOME NOVEL IMIDAZOPYRIDINES<br/>[FR] NOUVELLES IMIDAZOPYRIDINES ET LEUR UTILISATION
  申请人：ASTRAZENECA AB

  公开号：WO2004016611A1

  公开（公告）日：2004-02-26

  The use of compounds of formula (I) wherein R1, R3, R10, m and Ar are as defined in the Specification and pharmaceutically acceptable salts thereof in the manufacture of a medicament for the treatment or prophylaxis of diseases or conditions in which inhibition of kinase Itk activity is beneficial is disclosed. Certain novel compounds of formula (I), together with processes for their preparation, compositions containing them and their use in therapy are also disclosed.

  公开了在制备药物用于治疗或预防抑制激酶Itk活性有益的疾病或症状中，使用式(I)中R1、R3、R10、m和Ar所定义的化合物及其药学上可接受的盐。还公开了式(I)的某些新化合物，以及它们的制备方法、含有它们的组合物和它们在治疗中的用途。
• Synthesis of Fused Imidazoles and Benzothiazoles from (Hetero)Aromatic <i>ortho</i>-Diamines or <i>ortho</i>-Aminothiophenol and Aldehydes Promoted by Chlorotrimethylsilane
  作者：Dmitriy Volochnyuk、Sergey Ryabukhin、Andrey Plaskon、Andrey Tolmachev

  DOI：10.1055/s-2006-950289

  日期：2006.11

  New convenient conditions for benzimidazole and benzothiazole syntheses are described. A set of benzimidazoles, 3H-imidazo[4,5-b]pyridines, purines, xanthines and benzothiazoles was readily prepared from (hetero)aromatic ortho-diamines or ortho-aminothiophenol and aldehydes using chlorotrimethylsilane in DMF as a promoter and water-acceptor agent, followed by oxidation with air oxygen.

  描述了苯并咪唑和苯并噻唑合成的新便利条件。一组苯并咪唑、3H-咪唑并[4,5-b]吡啶、嘌呤、黄嘌呤和苯并噻唑很容易由（杂）芳族邻二胺或邻氨基苯硫酚和醛在 DMF 中使用三甲基氯硅烷作为促进剂和水受体制备剂，然后用空气氧氧化。
• Synthesis of 2-phenyl-1H-imidazo[4,5-b]pyridine as type 2 diabetes inhibitors and molecular docking studies
  作者：Muhammad Taha、Nor Hadiani Ismail、Syahrul Imran、Izzatul Ainaa、Manikandan Selvaraj、Mohd syukri baharudin、Muhammad Ali、Khalid Mohammed Khan、Nizam Uddin

  DOI：10.1007/s00044-017-1806-0

  日期：2017.5

  A series of imidazo[4,5-b]pyridines (3–32) was synthesized and evaluated for their ability to inhibit Baker’s yeast α-glucosidase enzyme. The IC50 values for all compounds were in the range of 13.5–93.7 µM with compound 15, a 2,4-dihydroxy-substituted analog, displayed the most potent activity potential. Structure–activity relationship strongly suggested the presence of hydroxyl group at aromatic side

  一系列咪唑并[4,5的b ]吡啶（3 - 32）合成并评价它们抑制面包酵母能力α葡糖苷酶的酶。所有化合物的IC 50值均在13.5–93.7 µM的范围内，其中化合物15是2,4-二羟基取代的类似物，具有最大的活性潜力。结构与活性之间的关系强烈表明，芳香族侧链上存在羟基是导致抑制潜力的主要因素。研究结果还表明，在邻位和对位具有羟基的化合物能够抑制α-葡糖苷酶有效。该实验观察得到了对人肠道麦芽糖酶-葡糖淀粉酶（PDB ID：3TOP）的对接研究的进一步支持。化合物15的咪唑并吡啶的–NH–基与Asp1526形成氢键，而邻苯二酚的两个羟基与Asp1279形成H键。咪唑并吡啶环通过与Phe1560的π - π堆积以及其他与Pro1159，Tyr1167，Asp1157，Met1421，Trp1369，Pro1318和Lys1460的侧链有关的疏水相互作用而得到很好的稳定。邻苯二酚环还与Phe15
• Bicyclic derivative, its production and use
  申请人：Oda Tsuneo

  公开号：US20050101647A1

  公开（公告）日：2005-05-12

  The present invention provides a heterocyclic compound having potent tyrosine kinase-inhibiting activity represented by formula: (wherein, R 1b is a C 6-10 aryl group which has substituent(s), and the like; T a is a single bond, a C 1-6 alkyl group, —CH 2 O—, and the like; X and Y are the same or different, and each is a nitrogen atom which may have substituent(s), and the like; the broken line is a single bond or a double bond; Z a is a nitrogen atom or CH; W is a single bond, an oxygen atom, and the like; Q is a C 6-10 aryl group which may have substituent(s) or an aromatic heterocyclic group which may have substituent(s)); or a salt thereof and a pharmaceutical composition comprising thereof.

  本发明提供了一种具有强效酪氨酸激酶抑制活性的杂环化合物，其化学式表示为：（其中，R1是具有取代基的C6-10芳基基团等；Ta是单键，C1-6烷基基团，—CH2O—等；X和Y相同或不同，每个都是氮原子，可以具有取代基等；断裂线是单键或双键；Z是氮原子或CH；W是单键，氧原子等；Q是具有取代基的C6-10芳基基团或具有取代基的芳香杂环基团）或其盐以及含有该化合物的药物组合物。
• Use of and some novel imidazopyridines
  申请人：Johansson Henrik

  公开号：US20050261333A1

  公开（公告）日：2005-11-24

  The use of compounds of formula (I) wherein R 1 , R 3 , R 10 , m and Ar are as defined in the Specification and pharmaceutically acceptable salts thereof in the manufacture of a medicament for the treatment or prophylaxis of diseases or conditions in which inhibition of kinase Itk activity is beneficial is disclosed. Certain novel compounds of formula (I), together with processes for their preparation, compositions containing them and their use in therapy are also disclosed.

  本发明揭示了在制造用于治疗或预防抑制酪氨酸激酶Itk活性对疾病或病况有益的药物时，使用公式（I）中R1、R3、R10、m和Ar定义的化合物及其药学上可接受的盐。本发明还揭示了某些新型公式（I）化合物及其制备方法、含有它们的组合物以及它们在治疗中的应用。