2-(2-methoxyphenyl)-3H-imidazo[4,5-c]pyridine | 87359-17-9

• 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-(2-methoxyphenyl)-3H-imidazo[4,5-c]pyridine
• CAS: 87359-17-9
• 化学式: C₁₃H₁₁N₃O
• mdl: MFCD19467365
• 分子量: 225.25
• InChiKey: JDGOSMKPJJSUMR-UHFFFAOYSA-N

物化性质

• 沸点：
  468.7±51.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 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：

  2-(2-methoxyphenyl)-3H-imidazo[4,5-c]pyridine 、 alkaline earth salt of/the/ methylsulfuric acid 生成 2-(2-Methoxyphenyl)-5-[[4-(trifluoromethoxy)phenyl]methyl]imidazo[4,5-c]pyridine
  参考文献：
  名称：

  抗病毒的2,5-二取代的咪唑并[4,5-c]吡啶类化合物：抗丙型肝炎病毒活性的进一步优化。

  摘要：

  取代的5-苄基-2-苯基-5H-咪唑并[4,5-c]吡啶代表了一类新的对瘟病毒和丙型肝炎病毒（HCV）具有活性的化合物。制备了几个在位置2和5上具有取代基修饰的类似物系列。这些努力导致发现了几种具有有效抗病毒活性的化合物，其中2-（2,3-二氟苯基）-5- [4-（三氟甲基）苄基] -5H-咪唑并[4,5-c]吡啶（46）对HCV最有效（EC（50）为0.10 microM，选择性指数为1080）。

  DOI：

  10.1016/j.bmcl.2007.07.015
• 作为产物：
  描述：

  邻甲氧基苯甲酸 、 3,4-二氨基吡啶 生成 2-(2-methoxyphenyl)-3H-imidazo[4,5-c]pyridine
  参考文献：
  名称：

  抗病毒的2,5-二取代的咪唑并[4,5-c]吡啶类化合物：抗丙型肝炎病毒活性的进一步优化。

  摘要：

  取代的5-苄基-2-苯基-5H-咪唑并[4,5-c]吡啶代表了一类新的对瘟病毒和丙型肝炎病毒（HCV）具有活性的化合物。制备了几个在位置2和5上具有取代基修饰的类似物系列。这些努力导致发现了几种具有有效抗病毒活性的化合物，其中2-（2,3-二氟苯基）-5- [4-（三氟甲基）苄基] -5H-咪唑并[4,5-c]吡啶（46）对HCV最有效（EC（50）为0.10 microM，选择性指数为1080）。

  DOI：

  10.1016/j.bmcl.2007.07.015

文献信息

• New imidazo[4,5-c]pyridine derivatives, processes for their preparation and pharmaceutical formulations containing such compounds
  申请人：MERCK PATENT GmbH

  公开号：EP0079083A1

  公开（公告）日：1983-05-18

  Compounds of formula (I'), and compositions containing them: (wherein n is 1, 2 or 3, each R1 independently represents a halogen atom; a hydroxy, carboxyl or C1-4 alkyl group, a C2-4 alkenyloxy, phenyl or phenyl-C1-4 alkoxy group which may be optionally substituted by one or more halogen atoms; an .amino, mono- or dialkyl-amino, morpholino or piperazino group; a group of formula -S(O)xRa where x is 0, 1 or 2 and Ra is a C1-4 alkyl group; or a C1-4 alkoxy group which may be optionally substituted by one or more radicals selected from hydroxy, C1-4 alkoxy, amino, mono- or di- C1-4 alkylamino, (phenyl- C1-4 alkyl)amino, N,N-C1-4alkyl(phenyl-C1-4alkyl)-amino and N,N-(C1-4alkoxyphenyl-C1-4alkyl)C1-4 alkyl-amino; n is 1, 2 or 3; m is 0 or 1; R2 represents a C1-4 alkyl group in the 1- or 3-position of the imidazo ring; R3 represents a hydrogen or halogen (fluorine, chlorine, bromine or iodine) atom, or a hydroxy, amino or C1-4 alkyl or alkoxy group; and physiologically acceptable acid addition salts thereof and N-oxides of such compounds and salts. Formula (1') includes the alternative tautomeric form. The compounds and compositions are useful for treatment of the human or animal body by therapy, particularly for use in the treatment or prophylaxis of heart failure and myocardial insufficiency.

  式(I')化合物及含有它们的组合物： (其中 n 为 1、2 或 3，每个 R1 独立地代表卤素原子；羟基、羧基或 C1-4 烷基、C2-4 烯氧基、苯基或苯基-C1-4 烷氧基，可任选被一个或多个卤素原子取代；.氨基、单或二烷基氨基、吗啉基或哌嗪基；式 -S(O)xRa 的基团，其中 x 为 0、1 或 2，Ra 为 C1-4 烷基；或 C1-4 烷氧基，可任选被一个或多个基团取代，这些基团选自羟基、C1-4 烷氧基、氨基、单-或二-C1-4 烷基氨基、（苯基-C1-4 烷基）氨基、N,N-C1-4 烷基（苯基-C1-4 烷基）氨基和 N,N-（C1-4 烷氧基苯基-C1-4 烷基）C1-4 烷基氨基；n 为 1、2 或 3；m 为 0 或 1； R2 代表咪唑环 1 位或 3 位上的 C1-4 烷基； R3 代表氢原子或卤素（氟、氯、溴或碘）原子，或羟基、氨基或 C1-4 烷基或 烷氧基；及其生理上可接受的酸加成盐和此类化合物和盐的 N-氧化物。式（1'）包括另一种同分异构形式。这些化合物和组合物可用于人体或动物机体的治疗，特别是用于治疗或预防心力衰竭和心肌功能不全。
• Ground and excited state prototropism in 2-(2′-methoxyphenyl)-1H-imidazo[4,5-c]pyridine
  作者：M.M Balamurali、S.K Dogra

  DOI：10.1016/j.molstruc.2003.10.047

  日期：2004.3

  Absorption, fluorescence and fluorescence excitation spectra of 2-(2'-methoxyphenyl)-H-1-imidazole[4,5-c]pyridine (2-MPIP-c) have been studied in different solvents and at different acid-base concentrations. Single photon counting fluorescence spectroscopic measurements were carried out to find out the excited state lifetimes under the above environments. AMI semi-empirical quantum mechanical, as well as, electronic structure calculations using the Hartree-Fock (HF), and density functional theory (DFT) B3LYP with 6-31G** basis set using GAUSSIAN 98 program were carried out to supplement the experimental data. Spectral data in different solvents and theoretical calculations suggest the presence of only one species (a-1) of 2-MPIP-c in all the solvents. Out of five different possible monocations (MC's), only one MC (formed by protonating the benzimidazole N3 atom) is present in the aqueous solution, as well as, in different non-aqueous solvents. Nature of first excited sin-let state in neutral 2-MPIP-c and its MC are pi pi* and charge transfer, respectively. Only one dication (formed by protonating both the basic centers. benzimidazole N3 and pyridyl N5) and one kind of monoanion (formed by deprotonating >N-H) are present in the solution. pK(a) and pKa* for various equilibriums were determined and discussed. (C) 2003 Elsevier B.V. All rights reserved.
• US4603139A
  申请人：——

  公开号：US4603139A

  公开（公告）日：1986-07-29
• Antiviral 2,5-disubstituted imidazo[4,5-c]pyridines: Further optimization of anti-hepatitis C virus activity
  作者：Gerhard Puerstinger、Jan Paeshuyse、Susanne Heinrich、Joachim Mohr、Nicole Schraffl、Erik De Clercq、Johan Neyts

  DOI：10.1016/j.bmcl.2007.07.015

  日期：2007.9

  zo[4,5-c]pyridines represent a novel class of compounds with activity against pestiviruses and the hepatitis C virus (HCV). Several series of analogues with modifications of the substituents in positions 2 and 5 were prepared. These efforts resulted in the discovery of several compounds with potent antiviral activity of which 2-(2,3-difluorophenyl)-5-[4-(trifluoromethyl)benzyl]-5H-imidazo[4,5-c]pyridine

  取代的5-苄基-2-苯基-5H-咪唑并[4,5-c]吡啶代表了一类新的对瘟病毒和丙型肝炎病毒（HCV）具有活性的化合物。制备了几个在位置2和5上具有取代基修饰的类似物系列。这些努力导致发现了几种具有有效抗病毒活性的化合物，其中2-（2,3-二氟苯基）-5- [4-（三氟甲基）苄基] -5H-咪唑并[4,5-c]吡啶（46）对HCV最有效（EC（50）为0.10 microM，选择性指数为1080）。