4-(1H-imidazo[4,5-b]pyridin-2-yl)aniline | 95377-69-8

• 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-(1H-imidazo[4,5-b]pyridin-2-yl)aniline
• CAS: 95377-69-8
• 化学式: C₁₂H₁₀N₄
• mdl: MFCD09863985
• 分子量: 210.238
• InChiKey: NQZRUPQLXOGNTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 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：
  67.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1H-imidazo[4,5-b]pyridin-2-yl)aniline 在 sodium 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 (Z)-6-{[4-(1H-imidazo[4,5-b]pyridin-2-yl)phenylamino]methylene}-4H-1,2,4-triazepine-3,5,7(6H)-trione
  参考文献：
  名称：

  设计和合成新型咪唑并[4,5- b ]吡啶基化合物作为具有CDK9抑制活性的强效抗癌药

  摘要：

  设计，合成和筛选了新的咪唑并[4,5- b ]吡啶衍生物，它们对乳腺癌（MCF-7）和结肠癌（HCT116）癌细胞系具有抗癌活性。九种化合物（I，II，IIIa，IIIb，IV，VI，VIIa，VIII，IX）表现出显着的抗MCF-7活性，而六种化合物（I，VIIc，VIIe，VIIf，VIII，IX）表现出显着的抗MCF-7活性HCT116。 相对于索拉非尼（IC 50），显示出显着抗癌活性的化合物具有显着的CDK9抑制潜力（IC 50 = 0.63–1.32μM）。 = 0.76μM）。此外，进行了分子对接研究以说明CDK9活性位点中活性最高的化合物的结合模式，该模式揭示了相对于天然配体（T3C）优越的结合亲和力。

  DOI：

  10.1016/j.bioorg.2018.07.006
• 作为产物：
  描述：

  2,3-二氨基吡啶 、 对氨基苯甲酸 在 polyphosphoric acid 作用下， 反应 6.0h， 以90%的产率得到4-(1H-imidazo[4,5-b]pyridin-2-yl)aniline
  参考文献：
  名称：

  N-芳基2-芳氧基乙酰胺是一类新型的脂肪酸酰胺水解酶（FAAH）抑制剂。

  摘要：

  脂肪酸酰胺水解酶（FAAH）是开发用于治疗神经系统疾病的药物的有希望的目标。为了寻找新的FAAH抑制剂，我们确定了2g 2-（4-环己基苯氧基）-N-（3-（恶唑并[4,5-b]吡啶-2-基）苯基）乙酰胺，IC50为2.6 µM，开发有效的FAAH抑制剂的化学起点。初步的逐线优化得到2-i-（4-phenylphenoxy）-N-（3-（oxazolo [4,5-b] pyridin-2-yl）phenyl）乙酰胺4i，IC50为0.35 µM。

  DOI：

  10.1080/14756366.2016.1265520

文献信息

• [EN] ARYL-1,3-AZOLE DERIVATIVES AND METHODS FOR INHIBITING HEPARNASE ACTIVITY<br/>[FR] DERIVES D'ARYL-1,3-AZOLE ET PROCEDES PERMETTANT D'INHIBER L'ACTIVITE DE L'HEPARANASE
  申请人：IMCLONE SYSTEMS INC

  公开号：WO2005030206A1

  公开（公告）日：2005-04-07

  The present invention encompasses heparanase inhibitors, particularly to certain 2-substituted heteroaryl-fused and aryl-fused carbazole derivatives that inhibit heparanase, pharmaceutical compositions that contain the compounds, methods for making the compounds, and methods of treating heparanase-dependent diseases and conditions in mammals by administering a therapeutically effective amount of the compounds to the mammals.

  本发明涵盖了抑制肝素酶的抑制剂，特别是特定的2-取代杂芳基融合和芳基融合的咔唑衍生物，这些衍生物抑制肝素酶，包含这些化合物的药物组合物，制备这些化合物的方法，以及通过向哺乳动物施用这些化合物的治疗有效量来治疗依赖肝素酶的疾病和病况的方法。
• Carbon-13 NMR spectra of isomeric 2-arylimidazopyridines
  作者：A. V. Tretyakov、L. I. Rudaya、A. V. El'tsov、M. F. Larin、V. A. Lopyrev

  DOI：10.1002/mrc.1260230104

  日期：1985.1

  The 13C NMR spectra of some 2‐arylimidazo‐[4,5‐c]‐ and ‐[4,5‐b]‐pyridines and their protonated forms have been studied. The nitrogen atom of the pyridine ring has been shown to be the most basic nitrogen in these compounds.

  已经研究了一些 2-芳基咪唑-[4,5-c]-和-[4,5-b]-吡啶及其质子化形式的 13C NMR 光谱。吡啶环的氮原子已被证明是这些化合物中碱性最强的氮原子。
• Structure-guided design and development of novel benzimidazole class of compounds targeting DNA gyraseB enzyme of Staphylococcus aureus
  作者：Renuka Janupally、Variam Ullas Jeankumar、Karyakulam Andrews Bobesh、Vijay Soni、Parthiban Brindha Devi、Venkat Koushik Pulla、Priyanka Suryadevara、Keerthana Sharma Chennubhotla、Pushkar Kulkarni、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmc.2014.09.008

  日期：2014.11

  The gyraseB subunit of Staphylococcus aureus DNA gyrase is a well-established and validated target though less explored for the development of novel antimicrobial agents. Starting from the available structural information in PDB (3TTZ), we identified a novel series of benzimidazole used as inhibitors of DNA gyraseB with low micromolar inhibitory activity by employing structure-based drug design strategy. Subsequently, this chemical class of DNA gyrase inhibitors was extensively investigated biologically through in vitro assays, biofilm inhibition assays, cytotoxicity, and in vivo studies. The binding affinity of the most potent inhibitor 10 was further ascertained biophysically through differential scanning fluorimetry. Further, the most potent analogues did not show any signs of cardiotoxicity in Zebra fish ether-a-go-go-related gene (zERG), a major breakthrough among the previously reported cardiotoxic gyraseB inhibitors. (C) 2014 Elsevier Ltd. All rights reserved.
• 1-[4-(1H-Benzoimidazol-2-yl)-phenyl]-3-[4-(1H-benzoimidazol-2-yl)-phenyl]-urea derivatives as small molecule heparanase inhibitors
  作者：Weitao Pan、Hua-Quan Miao、Yong-Jiang Xu、Elizabeth C. Navarro、James R. Tonra、Erik Corcoran、Armin Lahiji、Paul Kussie、Alexander S. Kiselyov、Wai C. Wong、Hu Liu

  DOI：10.1016/j.bmcl.2005.09.069

  日期：2006.1

  A novel class of 1-[4-(1H-benzoimidazol-2-yl)-phenyl]-3-[4-(1H-benzoimidazol-2-yl)-phenyl]-ureas are described as potent inhibitors of heparanase. Among them are 1,3-bis-[4-(1H-benzoimidazol-2-yl)-phenyl]-urea (7a) and 1,3-bis-[4-(5,6-dimethyl-1H-benzoimidazol-2-yl)-phenyl]-urea (7d), which displayed good heparanase inhibitory activity (IC50 0.075-0.27 mu M). Compound 7a showed good efficacy in a B16 metastasis model. (c) 2005 Elsevier Ltd. All rights reserved.
• Tret'yakova, A. V.; Rudaya, L. I.; El'tsov, A. V., Journal of general chemistry of the USSR, 1984, vol. 54, # 11, p. 2338 - 2340
  作者：Tret'yakova, A. V.、Rudaya, L. I.、El'tsov, A. V.

  DOI：——

  日期：——

表征谱图