2-(4′-aminophenyl)-1H-imidazo[4,5-c]-pyridine | 75007-95-3

• 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′-aminophenyl)-1H-imidazo[4,5-c]-pyridine
• 英文别名: 4-(1(3)H-imidazo[4,5-c]pyridin-2-yl)-aniline；4-(1(3)H-Imidazo[4,5-c]pyridin-2-yl)-anilin；2-(4-amino-phenyl)-1H-imidazo[4,5-c]pyridine；4-(1H-imidazo[4,5-c]-pyridin-2-yl)-phenylamine；2-(4-aminophenyl)imidazo[4,5-c]pyridine；Benzenamine, 4-(1H-imidazo(4,5-c)pyridin-2-yl)-；4-(3H-imidazo[4,5-c]pyridin-2-yl)aniline
• CAS: 75007-95-3
• 化学式: C₁₂H₁₀N₄
• 分子量: 210.238
• InChiKey: UOLIKXCOOAWSDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：

  2-(4′-aminophenyl)-1H-imidazo[4,5-c]-pyridine 、 3-溴-4-甲氧基苯乙酸 在 N,N'-羰基二咪唑 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 25.5h， 以14%的产率得到2-(3-bromo-4-methoxy-phenyl)-N-[4-(1H-imidazo[4,5-c]-pyridin-2-yl)-phenyl]-acetamide
  参考文献：
  名称：

  [EN] ARYL-1,3-AZOLE DERIVATIVES AND METHODS FOR INHIBITING HEPARNASE ACTIVITY
  [FR] DERIVES D'ARYL-1,3-AZOLE ET PROCEDES PERMETTANT D'INHIBER L'ACTIVITE DE L'HEPARANASE

  摘要：

  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。

  公开号：

  WO2005030206A1
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 、 copper diacetate 作用下， 生成 2-(4′-aminophenyl)-1H-imidazo[4,5-c]-pyridine
  参考文献：
  名称：

  Weidenhagen; Weeden, Chemische Berichte, 1938, vol. 71, p. 2347,2358

  摘要：

  DOI：

文献信息

• [EN] TRICYCLIC INHIBITORS OF KINASES USEFUL FOR THE TREATMENT OF PROLIFERATIVE DISEASES<br/>[FR] INHIBITEURS TRICYCLIQUES DE KINASES UTILES POUR LE TRAITEMENT DES MALADIES PROLIFÉRATIVES
  申请人：ABBOTT LAB

  公开号：WO2013012681A1

  公开（公告）日：2013-01-24

  The present invention relates to compounds of formula (I) or pharmaceutical acceptable salts, wherein R1, R2, R3, A, B, and n are defined in the description. The present invention relates also to compositions containing said compounds which are useful for inhibiting kinases such as wee-1 and methods of treating diseases such as cancer.

  本发明涉及式(I)的化合物或药用可接受的盐，其中R1、R2、R3、A、B和n在描述中有定义。本发明还涉及含有上述化合物的组合物，用于抑制wee-1等激酶以及治疗癌症等疾病的方法。
• Synthesis of imidazo[4,5-<i>b</i>]- and [4,5-<i>c</i>]pyridines
  作者：Richard W. Middleton、D. George Wibberley

  DOI：10.1002/jhet.5570170824

  日期：1980.12

  2-Arylimidazo[4,5-b]- and [4,5-c]pyridines have been prepared by treatment of the appropriate 2,3- or 3,4-diaminopyridine with an aromatic carboxylic acid in the presence of polyphosphoric acid. Other derivatives have been prepared by similar cyclisation of diaminopyridines using triethyl orthoformate, urea, thiophosgene and thiourea and the properties of some N-oxides have been investigated. A number

  通过在多磷酸存在下用芳族羧酸处理适当的2,3-或3,4-二氨基吡啶，可以制备2-Arylimidazoazo [4,5- b ]-和[4,5- c ]吡啶。使用原甲酸三乙酯，尿素，硫光气和硫脲，通过二氨基吡啶的类似环化反应，已经制备了其他衍生物，并且已经研究了一些N-氧化物的性质。已经筛选了许多芳基咪唑并吡啶的致突变性。
• Photophysics of 2-(4′-Amino-2′-hydroxyphenyl)-1<i>H</i>-imidazo-[4,5-<i>c</i>]pyridine and Its Analogues: Intramolecular Proton Transfer versus Intramolecular Charge Transfer
  作者：Santosh Kumar Behera、Ananda Karak、G. Krishnamoorthy

  DOI：10.1021/jp5064808

  日期：2015.2.12

  processes, the photophysical properties of 2-(4′-amino-2′-methoxyphenyl)-1H-imidazo-[4,5-c]pyridine (AMPIP-c) and 2-(4′-aminophenyl)-1H-imidazo-[4,5-c]pyridine (APIP-c) were also investigated. Though APIP-c displays twisted ICT (TICT) emission in protic solvents, AHPIP-c exhibits normal and tautomer emissions in aprotic as well as in protic solvents due to ESIPT. However, the methoxy derivative, AMPIP-c

  2-（4'-氨基-2'-羟基苯基）-1 H-咪唑-[4,5- c ]吡啶（AHPIP-c）的光物理特性已在各种质子惰性和质子传递溶剂中使用紫外可见，稳定的溶液进行了研究。状态荧光和时间分辨荧光光谱技术。为了理解分子内电荷转移（ICT）和激发态分子内质子转移（ESIPT）过程之间的竞争，2-（4'-氨基-2'-甲氧基苯基）-1 H-咪唑-[4， 5- c ]吡啶（AMPIP-c）和2-（4'-氨基苯基）-1 H-咪唑-[4,5- c还研究了吡啶（APIP-c）。尽管APIP-c在质子传递溶剂中显示出扭曲的ICT（TICT）排放，但由于ESIPT，AHPIP-c在质子传递以及质子传递中表现出正常和互变异构体排放。但是，甲氧基衍生物AMPIP-c在甲醇中发出微弱的TICT荧光。
• Pyridine compounds
  申请人：ELI LILLY AND COMPANY

  公开号：EP0093593A2

  公开（公告）日：1983-11-09

  This invention provides compounds for use as positive inotropic agents, bronchodilators, vasodilators and anticoagulants of the formula: or a pharmaceutically acceptable salt thereof, wherein R, is hydrogen, C1-C4 alkyl, or chloro; R2 and R3 are independently hydrogen, C1-C4 alkyl, C1-C4 alkoxy, allyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, hydroxy, halo, cyano, nitro, amino, mono- or di-(C1-C4 alkyl)amino, trifluoromethyl, or C1-C4 alkoxy substituted with a group Z-Q-, wherein Q is oxygen, sulfur, sulfinyl, sulfonyl, or a bond, and Z is a C1-C4 alkyl, phenyl, or phenyl substituted with halo, C1-C4 alkyl, C1-C4 alkoxy, hydroxy, nitro, amino, C1-C4 alkylthio, C1-C4 alkylsulfinyl, or C1-C4 alkylsulfonyl; and R4 is hydrogen, C1-C4 alkyl, or C1-C4 alkoxy; with the provisions that: a) if R, and two of R2, R3, and R4 are all hydrogen, the other of R2, R3, and R4 is not hydrogen, halo, hydroxy, nitro, amino, di-(C,-C2 alkyl)amino, or C1-C2 alkoxy; b) if R, and one of R2, R3 and R4 are both hydrogen, and one of R2, R3 and R4 is C1-C2 alkoxy, the other of R2, R3 and R4 is not hydroxy or C1-C2 alkoxy; c) if R, is chloro and two of R2, R3, and R4 are all hydrogen, the other of R2, R3, and R4 is not hydrogen, halo, C1-C2 alkyl, or nitro; and d) if R, is chloro and R4 is hydrogen, R2 and R3 may not both be nitro.

  这项发明提供了以下公式的化合物，用作正性肌力药物、支气管扩张剂、血管扩张剂和抗凝剂，或其药学上可接受的盐：其中R是氢、C1-C4烷基或氯；R2和R3独立地是氢、C1-C4烷基、C1-C4烷氧基、烯丙氧基、C1-C4烷硫基、C1-C4烷基亚砜基、C1-C4烷基磺酰基、羟基、卤素、氰基、硝基、氨基、单-或双-(C1-C4烷基)氨基、三氟甲基或C1-C4烷氧基取代的Z-Q-基团，其中Q是氧、硫、亚砜基、磺酰基或键，Z是C1-C4烷基、苯基或取代有卤素、C1-C4烷氧基、羟基、硝基、氨基、C1-C4烷硫基、C1-C4烷基亚砜基或C1-C4烷基磺酰基的苯基；和R4是氢、C1-C4烷基或C1-C4烷氧基；但需满足以下条件：a）如果R和R2、R3和R4中的两个都是氢，则R2、R3和R4中的另一个不是氢、卤素、羟基、硝基、氨基、双-(C1-C2烷基)氨基或C1-C2烷氧基；b）如果R和R2、R3和R4中的一个都是氢，而R2、R3和R4中的一个是C1-C2烷氧基，则R2、R3和R4中的另一个不是羟基或C1-C2烷氧基；c）如果R是氯，而R2、R3和R4中有两个都是氢，则R2、R3和R4中的另一个不是氢、卤素、C1-C2烷基或硝基；d）如果R是氯，而R4是氢，则R2和R3不能同时为硝基。
• 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.