2-(2'-hydroxyphenyl)-3H-imidazo[4,5-b]pyridine | 24192-87-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2'-hydroxyphenyl)-3H-imidazo[4,5-b]pyridine
• 英文别名: 2-(3H-Imidazo[4,5-b]pyridin-2-yl)-phenol；2-(1H-imidazo[4,5-b]pyridin-2-yl)phenol
• CAS: 24192-87-8
• 化学式: C₁₂H₉N₃O
• 分子量: 211.223
• InChiKey: TXIZWDGGKIUXDT-UHFFFAOYSA-N

物化性质

• 熔点：
  323-325 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  404.6±47.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：
  61.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-(2'-hydroxyphenyl)-3H-imidazo[4,5-b]pyridine 在 sodium hydroxide 作用下， 以 水 为溶剂， 以83%的产率得到2-(2-acetoxyphenyl)-1H-imidazo<4,5-b>pyridine
  参考文献：
  名称：

  咪唑并吡啶抑制环核苷酸磷酸二酯酶：舒马唑和异唑的类似物作为cGMP特异性磷酸二酯酶的抑制剂。

  摘要：

  描述了一系列咪唑并吡啶（包括舒马唑和异唑）对分离的PDE同工酶的合成和磷酸二酯酶（PDE）抑制谱。结果表明，舒马唑和异咪唑都是PDE III的弱抑制剂，它们的正性活性不太可能仅由于PDE III的抑制而引起。出乎意料的是，发现这两种化合物都是cGMP特异性同工酶PDE V的重要抑制剂，并且已经制备了一系列简单的2-取代的苯基咪唑并[4,5-b]吡啶用于研究PDE活性的SAR。已显示这对链长，极性和杂原子连接基团的性质敏感。已经确定了有效的PDE V抑制剂，其中许多也是PDE IV的重要抑制剂。

  DOI：

  10.1021/jm00062a011
• 作为产物：
  描述：

  2,3-二氨基吡啶 、 水杨酸 在 polyphosphoric acid 作用下， 反应 2.0h， 生成 2-(2'-hydroxyphenyl)-3H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  2-（2'-羟基苯基）咪唑并[4,5- b ]吡啶的光诱导质子和电荷转移

  摘要：

  本文研究了2-（2'-羟苯基）咪唑并[4,5- b ]吡啶（1）的溶剂性质与异构之间的相互作用，以及不同异构体在第一代中所经历的质子和电荷转移过程。兴奋的单重态。我们证明了这些过程对1的荧光性能的强大影响。我们通过紫外可见吸收光谱以及稳态和时间分辨荧光光谱研究了几种中性和酸化溶剂中1的行为。1的荧光对环境表现出强烈的敏感性。这种行为是构象和异构体平衡以及异构体完全不同的激发态行为的结果。对于中性和阳离子1而言，在羟基和苯并咪唑N之间具有分子内氢键的异构体均经历超快激发态分子内质子转移（ESIPT），产生具有非常大的斯托克斯位移的互变异构物质。对于中性和阳离子1，与氢键合到溶剂上的OH基团的异构体表现为强光酸，在具有碱性特征的溶剂中以激发态解离。吡啶氮具有光碱特性，即使在某些中性溶剂中也处于激发态的质子化状态。检测到了几种有效的无辐射失活通道，我们将其归因于扭曲的分子内电荷转移（TICT）过

  DOI：

  10.1021/jp311709c

文献信息

• 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。
• Ester derivatives of dimethylpropionic acid and pharmaceutical compositions containing them
  申请人：CERMOL S.A.

  公开号：EP1132381A1

  公开（公告）日：2001-09-12

  The present invention relates to esters of 2,2-dimethylpropionic acid having the general formula (I) or pharmacological acceptable salts thereof, as well as to pharmaceutical compositions containing said compounds and having an inhibitory activity of elastase.

  本发明涉及具有通式（I）的2,2-二甲基丙酸酯或其药理学上可接受的盐，以及含有该化合物并具有弹性蛋白酶抑制活性的药物组合物。
• 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：——
• Microwave-assisted one step high-throughput synthesis of benzimidazoles
  作者：Shou-Yuan Lin、Yuko Isome、Ethan Stewart、Ji-Feng Liu、Daniel Yohannes、Libing Yu

  DOI：10.1016/j.tetlet.2006.02.127

  日期：2006.4

  One-pot synthesis of benzimidazoles from diamines and carboxylic acids was developed under microwave irradiation condition, which provided a practical and efficient method for high-throughput synthesis of this important class of heterocyclic compounds. (c) 2006 Elsevier Ltd. All rights reserved.
• Enhancing Excited State Intramolecular Proton Transfer in 2-(2′-Hydroxyphenyl)benzimidazole and Its Nitrogen-Substituted Analogues by β-Cyclodextrin: The Effect of Nitrogen Substitution
  作者：Francis A. S. Chipem、Santosh Kumar Behera、G. Krishnamoorthy

  DOI：10.1021/jp311438s

  日期：2013.5.23

  Excited state intramolecular proton transfer (ESIPT) in nitrogen-substituted analogues of 2-(2'-hydroxyphenyl)benzimidazole (HPBI), 2-(2'-hydroxyphenyl)-3H-imidazo[4,5-b]pyridine (HPIP-b), and 2-(2'-hydroxyphenyl)-3H-imidazo[4,5-c]pyridine (HPIP-c) have been investigated in a beta-cyclodextrin (beta-CD) nanocavity and compared with that of HPBI. The stoichiometry and the binding constants of the complexes were determined by tautomer emissions. Both pK(a) and NMR experiments were employed to determine the orientation of the molecules inside of the beta-CD cavity. Huge enhancement in the tautomer emission of HPIP-b and HPIP-c compared to that of HPBI in beta-CD suggests that not only is the ESIPT favored inside of the cavity, but also, the environment reduces the nonradiative decay through the formation of an intramolecular charge-transfer (ICT) state. Unlike HPBI, the tautomer emission to normal emission ratio of HPIP-b increases from 0.9 to 2.6, and that of HPIP-c increases from 4.9 to 7.4 in 15 mM beta-CD. The effect of dimethylsulfoxide (DMSO) on complexation was also investigated for all three guest molecules. In DMSO, HPBI is present in neutral form, but the nitrogen-substituted analogues are present in both neutral and monoanionic forms. However, in DMSO upon encapsulation by beta-CD, all three molecules are present in both neutral and monoanionic forms in the nanocavity. The monoanion is stabilized more inside of the beta-CD cavity. The studies revealed that the ESIPT of nitrogen-substituted analogues is more susceptible to the environment than HPBI, and therefore, they are more promising probes.

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