2-(1H-benzoimidazol-2-yl)pyridin-3-ol | 5004-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(1H-benzoimidazol-2-yl)pyridin-3-ol
• 英文别名: 3-Pyridinol, 2-(1H-benzimidazol-2-yl)-；2-(1H-benzimidazol-2-yl)pyridin-3-ol
• CAS: 5004-83-1
• 化学式: C₁₂H₉N₃O
• 分子量: 211.223
• InChiKey: SRYNFTOUOFLELK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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

• 作为产物：
  描述：

  3-羟基-2-吡啶甲酸 、 邻苯二胺 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 4.0h， 生成 2-(1H-benzoimidazol-2-yl)pyridin-3-ol
  参考文献：
  名称：

  CuI-catalyzed hydroxylation of aryl bromides under the assistance of 5-bromo-2-(1H-imidazol-2-yl)pyridine and related ligands

  摘要：

  A number of substituted 2-pyridin-2-yl-1H-benzoimidazoles and 2-(1H-imidazol-2-yl)pyridines were screened for promoting CuI-catalyzed hydroxylation of aryl bromides, which led to the discovery of the combination of Cut and 5-bromo-2-(1H-imidazol-2-yl)pyridine as an effective catalytic system for this transformation. Both electron-rich and electronic-deficient aryl bromides could be converted into the corresponding substituted phenols in good to excellent yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.059

文献信息

• Metal-Mediated Inhibition of <i>Escherichia </i><i>c</i><i>oli</i> Methionine Aminopeptidase:  Structure−Activity Relationships and Development of a Novel Scoring Function for Metal−Ligand Interactions
  作者：Rolf Schiffmann、Alexander Neugebauer、Christian D. Klein

  DOI：10.1021/jm050476z

  日期：2006.1.1

  We report the discovery of thiabendazole as a potent inhibitor (K-i = 0.4 mu M) of Escherichia coli methionine aminopeptidase (ecMetAP) and the synthesis and pharmacological evaluation of thiabendazole congeners with activity in the upper nanomolar range. Elucidation of the X-ray structure of ecMetAP in complex with thiabendazole and an unrelated inhibitor that was independently described by another group showed that that both compounds bind to an additional Coll ion at the entrance of the active site. This unexpected finding explains the inactivity of the compounds under in vivo conditions. It also allows us to discuss the structure-activity relationships of this series of compounds in a meaningful way, based upon docking runs with an auxiliary metal ion. We describe a new scoring function for the evaluation of metal-mediated inhibitor binding that, unlike the previously used scoring function implemented in the docking program, allows us to distinguish between active and inactive compounds. Finally, conclusions for the structure-based design of in vivo-active inhibitors of ecMetAP are drawn.
• Ground- and Excited-State Tautomerism in 2-(3'-Hydroxy-2'-pyridyl)benzimidazole
  作者：Flor Rodriguez Prieto、M. Carmen Rios Rodriguez、M. Mosquera Gonzalez、Miguel A. Rios Fernandez

  DOI：10.1021/j100086a014

  日期：1994.9
• CuI-catalyzed hydroxylation of aryl bromides under the assistance of 5-bromo-2-(1H-imidazol-2-yl)pyridine and related ligands
  作者：Jianhuan Jia、Chenglin Jiang、Xiaojing Zhang、Yongwen Jiang、Dawei Ma

  DOI：10.1016/j.tetlet.2011.08.059

  日期：2011.10

  A number of substituted 2-pyridin-2-yl-1H-benzoimidazoles and 2-(1H-imidazol-2-yl)pyridines were screened for promoting CuI-catalyzed hydroxylation of aryl bromides, which led to the discovery of the combination of Cut and 5-bromo-2-(1H-imidazol-2-yl)pyridine as an effective catalytic system for this transformation. Both electron-rich and electronic-deficient aryl bromides could be converted into the corresponding substituted phenols in good to excellent yields. (C) 2011 Elsevier Ltd. All rights reserved.