2-(6'-hydroxy-2'-pyridyl)benzimidazole | 74356-83-5

• 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-(6'-hydroxy-2'-pyridyl)benzimidazole
• 英文别名: 2(1H)-Pyridinone, 6-(1H-benzimidazol-2-yl)-；6-(1H-benzimidazol-2-yl)-1H-pyridin-2-one
• CAS: 74356-83-5
• 化学式: C₁₂H₉N₃O
• 分子量: 211.223
• InChiKey: BVNZJHVZTWOXDY-UHFFFAOYSA-N

物化性质

• 熔点：
  284-285 °C
• 密度：
  1.376±0.06 g/cm3(Predicted)

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：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [RuHCl(CO)(PPh₃)₃] 、 2-(6'-hydroxy-2'-pyridyl)benzimidazole 以 二氯甲烷 为溶剂， 反应 24.0h， 以72%的产率得到C₄₉H₄₀N₃O₂P₂Ru⁽¹⁺⁾*Cl^(1-)
  参考文献：
  名称：

  钌配合配合物催化嘧啶的多组分合成。

  摘要：

  合成和表征了一套新的基于2-（2-苯并咪唑基）吡啶配体的空气和湿气稳定的钌配合物。直接从各种am，伯醇和仲醇直接合成高度取代的嘧啶，对这些配合物的催化行为进行了评估。在所有金属配合物中，含有配合物A的2-羟基吡啶和苯并咪唑片段在该反应中显示出最佳的反应性。另外，观察到苯并咪唑的NH质子和吡啶的羟基在增强催化活性中起关键作用。进行了一些对照实验和机理研究，以了解使用配合物A进行的嘧啶多组分合成。

  DOI：

  10.1039/c9dt04040d
• 作为产物：
  描述：

  6-甲氧基吡啶-2-甲酸 在 PPA 、 氢溴酸 作用下， 反应 4.0h， 生成 2-(6'-hydroxy-2'-pyridyl)benzimidazole
  参考文献：
  名称：

  一些2-（取代的吡啶基）苯并咪唑类化合物的合成和抗炎活性。

  摘要：

  合成了一系列的2-（2-吡啶基）苯并咪唑，并通过角叉菜胶诱导的大鼠爪水肿试验评估了其抗炎活性。在几种活性衍生物中，选择2-（5-乙基吡啶-2-基）苯并咪唑（6）进行进一步研究。化合物6与苯基丁a和噻草胺的比较表明，在急性炎症模型中，化合物6具有比苯基丁a和噻草胺稍强的胃肠道刺激性。

  DOI：

  10.1021/jm00181a007

文献信息

• A three-dimensional silver(I) coordination polymer involving a new bridging mode of saccharinate
  作者：Emel Guney、Veysel T. Yilmaz、Orhan Buyukgungor

  DOI：10.1016/j.inoche.2010.02.005

  日期：2010.4

  three-dimensional silver(I)-saccharinato (sac) coordination polymer [Ag2(μ-sac)2]n has been synthesized and characterized by elemental analysis, IR and single crystal X-ray diffraction. The silver(I) ions are doubly bridged by the imino N and carbonyl O atoms of two sac ligands, leading to a dimer [Ag2(μ-sac)2] with a very short Ag–Ag contact of 2.8622(6) A. The dimeric units are linked by unique Ag–Csac

  摘要 合成了一种三维银(I)-糖精(sac)配位聚合物[Ag2(μ-sac)2]n，并通过元素分析、红外和单晶X射线衍射对其进行了表征。银 (I) 离子被两个囊配体的亚氨基 N 和羰基 O 原子双桥接，导致二聚体 [Ag2(μ-sac)2] 与非常短的 Ag-Ag 接触 2.8622(6) A。二聚单元通过独特的 Ag–Csac (η1) 键连接成二维梯状层，这些层通过弱 Ag⋯O(sulphonyl) 和 π(sac)⋯π(sac) 进一步组装成三维网络) 互动。复合物 1 是涉及 η1 Ag-C 键的聚合物网络的第一个例子。除了囊的新配位模式外，还讨论了复合物的红外光谱和热性质。
• 2-(2-Benzimidazolyl)pyridine Mn(I) Complexes: Synthesis and Exploration of Catalytic Activity toward Synthesis of Pyrimidine and Quinoline
  作者：Srabani Nandi、Ishani Borthakur、Kasturi Ganguli、Sabuj Kundu

  DOI：10.1021/acs.organomet.3c00034

  日期：2023.7.24

  them, Mn1 complex bearing a proton-responsive 2-hydroxypyridine-appended benzimidazole ligand was found to be highly effective for the synthesis of different N-heterocycles utilizing alcohols. Employing significantly lower catalyst loading (0.05 mol %), several substituted pyrimidines and quinolines were effectively synthesized. The lactim–lactam acid–base equilibrium of the 2-hydroxypyridine fragment

  合成了一系列不含膦的苯并咪唑和含吡啶的二齿Mn(I)配合物。其中，带有质子响应性2-羟基吡啶附加苯并咪唑配体的Mn1配合物被发现对于利用醇合成不同的N-杂环非常有效。采用显着较低的催化剂负载量（0.05 mol%），有效合成了几种取代的嘧啶和喹啉。研究了2-羟基吡啶片段的内酰胺-内酰胺酸碱平衡、碱的抗衡阳离子的作用以及外部添加的配体的影响。基于各种控制实验和不同的动力学研究，提出了可能的催化循环。
• 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.
• On the Mechanism of Alcohol-Catalyzed Excited-State Intramolecular Proton Transfer in Cationic Benzimidazoles
  作者：M. Carmen Ríos Rodríguez、J. Carlos Penedo、Robert J. Willemse、Manuel Mosquera、Flor Rodríguez-Prieto

  DOI：10.1021/jp991375d

  日期：1999.9.1

  The ground- and excited-state behavior of the monocations of 2-(6'-hydroxy-2'-pyridyl)benzimidazole (1) and 1-methyl-2-(6'-hydroxy-2'-pyridyl)benzimidazole (2) is discussed. Excited-stale proton transfer from the hydroxyl group to the pyridyl nitrogen occurs in compounds 1 and 2 in acidified acetonitrile solutions by the assistance of an alcohol. We propose a model for the mechanism of this proton-transfer process which includes a concerted biprotonic or multiprotonic transfer with one or two alcohol molecules. Essential for the occurrence of the proton transfer is the presence of a quencher with hydrogen-bond donating and accepting properties. Furthermore, it is shown that also the size and geometry of the quencher play a role in the efficiency of the proton-transfer process. Compounds 1 and 2 differ remarkably in the efficiency of this processes a result of the presence of the methyl group on the benzimidazole nitrogen N(1) in compound 2.