5-methyl-2-(2'-pyridyl)benzimidazole | 7471-12-7

• 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: 5-methyl-2-(2'-pyridyl)benzimidazole
• 英文别名: 5-methyl-2-(pyridin-2-yl)-1H-benzo[d]imidazole；6-methyl-2-pyridin-2-yl-1H-benzimidazole
• CAS: 7471-12-7
• 化学式: C₁₃H₁₁N₃
• 分子量: 209.25
• InChiKey: HFYFOFMVURXVSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 储存条件：
  -20°C

制备方法与用途

ecMetAP-IN-1（化合物17）是一种有效的ecMetAP抑制剂，其IC50值为2.086 µM。

反应信息

• 作为反应物：
  描述：

  5-methyl-2-(2'-pyridyl)benzimidazole 在 palladium on activated charcoal 硫酸 、 氢气 、 溴 、 硝酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 110.0 ℃ 、344.74 kPa 条件下， 反应 12.67h， 生成 5-Methyl-2-pyridin-2-yl-1H-benzoimidazol-4-ylamine
  参考文献：
  名称：

  Differential antiproliferative activity of new benzimidazole-4,7-diones

  摘要：

  Ten benzimidazole-4,7-diones were synthesized and tested in vitro on two tumor cell lines. Several compounds showed a significant antiproliferative activity on K562 cells, although to a different extent, whereas compound 1i showed a highly significant activity on SW620 cells, comparable to that of doxorubicin. Both the substituents in the quinone ring and the position of the nitrogen atom in the pyridine moiety play a crucial role for the biological activity.

  DOI：

  10.1016/j.farmac.2004.04.001
• 作为产物：
  描述：

  5-Methyl-2-pyridin-2-yl-1-(2-pyridin-4-ylethyl)benzimidazole 在 三氯化铝 作用下， 以 various solvent(s) 为溶剂， 反应 0.5h， 生成 5-methyl-2-(2'-pyridyl)benzimidazole
  参考文献：
  名称：

  Ichikawa, Masataka; Yamamoto, Chiyuki; Hisano, Takuzo, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 10, p. 3042 - 3047

  摘要：

  DOI：

文献信息

• Two new Cu(II) dipeptide complexes based on 5-methyl-2-(2′-pyridyl)benzimidazole as potential antimicrobial and anticancer drugs: Special exploration of their possible anticancer mechanism
  作者：Yong-Yu Qi、Qian Gan、Ya-Xian Liu、Ya-Hong Xiong、Zong-Wan Mao、Xue-Yi Le

  DOI：10.1016/j.ejmech.2018.05.023

  日期：2018.6

  In the search for more effective anticancer drugs with less toxic side effects, dipeptides were introduced into the Cu(II) complex of 5-methyl-2-(2′-pyridyl)benzimidazole (HPBM). Analytical and spectroscopic techniques were employed to thoroughly characterize complexes [Cu(Gly-gly)(HPBM)(H2O)]ClO4·0.5H2O (1) and [Cu(Gly-L-leu)(HPBM)(H2O)]ClO4 (2) (where Gly-gly = Glycyl-glycine anion, Gly-L-leu = Glycyl-l-leucine

  为了寻找更有效的抗癌药物，且毒副作用较小，将二肽引入了5-甲基-2-（2'-吡啶基）苯并咪唑（HPBM）的Cu（II）配合物中。采用分析和光谱技术对配合物[Cu（Gly-gly）（HPBM）（H 2 O）] ClO 4 ·0.5H 2 O（1）和[Cu（Gly- L -leu）（HPBM）（ ħ 2 O）] CLO 4（2）（其中，甘氨酸-甘氨酸=甘氨酰-甘氨酸阴离子，Gly-大号-leu =甘氨酰-升-亮氨酸阴离子）。通过紫外-可见（UV-Vis）光谱进行的溶液稳定性研究证实了缓冲液中复合物的稳定性。使用多光谱，粘度测量和分子对接方法评估了DNA结合亲和力，并进一步通过K b和K app值进行定量，揭示了嵌入模式。此外，凝胶电泳分析表明，在抗坏血酸存在下，复合物可能通过羟自由基途径破坏CT DNA。所有复合物对所测试的微生物（枯草芽孢杆菌，金黄色葡萄球菌，大肠杆菌）均表现出良好的抗菌和细
• 2-Substituted azole derivatives. 1. Synthesis and antiinflammatory activity of some 2-(substituted-pyridinyl)benzimidazoles
  作者：Goro Tsukamoto、Koichiro Yoshino、Toshihiko Kohno、Hiroshi Ohtaka、Hajime Kagaya、Keizo Ito

  DOI：10.1021/jm00181a007

  日期：1980.7

  A series of 2-(2-pyridinyl)benzimidazoles was synthesized and evaluated for antiinflammatory activity by the carrageenan-induced rat paw edema assay. Among several active derivatives, 2-(5-ethylpyridin-2-yl)benzimidazole (6) was selected for further study. A comparison of compound 6 with phenylbutazone and tiaramide revealed that 6 possesses stronger activity in acute inflammatory models possibly with

  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。
• NOVEL ONE-POT HOMOGENEOUS PROCESS FOR THE LARGE SCALE MANUFACTURE OF 2-SUBSTITUTED BENZIMIDAZOLES
  申请人：Ecolab USA Inc.

  公开号：US20190144395A1

  公开（公告）日：2019-05-16

  2-substituted benzimidazoles and methods of preparing the same are disclosed. The compositions may include a compound or salt thereof, an acid, and a polar aprotic solvent. The compositions may be used to inhibit corrosion of a metal surface in contact with an aqueous system, and provide enhanced protection against corrosion of metals in the aqueous system.

  揭示了2-取代苯并咪唑及其制备方法。这些组合物可能包括化合物或其盐、酸和极性无水溶剂。这些组合物可用于抑制与水系统接触的金属表面的腐蚀，并提供对水系统中金属腐蚀的增强保护。
• 2-Substituted Imidazole and Benzimidazole Corrosion Inhibitors
  申请人：Ecolab USA Inc.

  公开号：US20160348252A1

  公开（公告）日：2016-12-01

  Disclosed are methods of using nitrogen-containing compounds as corrosion inhibitors. The present method is used to inhibit corrosion of a metal surface in contact with an aqueous system using 2-substituted imidazoles and 2-substituted benzimidazoles, and provides enhanced protection against corrosion of metals in the aqueous system. The method comprises the use of corrosion inhibitors that are generally resistant to halogen attack and provide good corrosion resistance in the presence of oxidizing halogen-based biocides. Formulations comprising 2-substituted imidazoles and 2-substituted benzimidazoles are also disclosed.

  揭示了使用含氮化合物作为缓蚀剂的方法。本方法用于通过使用2-取代咪唑和2-取代苯并咪唑来抑制与水系接触的金属表面的腐蚀，并提供增强的金属在水系中的抗腐蚀保护。该方法包括使用通常对卤素攻击具有抵抗力并在存在氧化性卤素类生物杀菌剂时提供良好耐蚀性的缓蚀剂。还公开了包含2-取代咪唑和2-取代苯并咪唑的配方。
• Three new mixed‐ligand copper(II) complexes containing glycyl‐ <scp>l</scp> ‐valine and N,N‐aromatic heterocyclic compounds: Synthesis, characterization, DNA interaction, cytotoxicity and antimicrobial activity
  作者：Yong‐Yu Qi、Ya‐Xian Liu、Qian Gan、Ya‐Hong Xiong、Zong‐Wan Mao、Xue‐Yi Le

  DOI：10.1002/aoc.4126

  日期：2018.3

  Three novel copper(II) complexes, [Cu(Gly‐l‐Val)(HPBM)(H2O)]·ClO4·H2O (1), [Cu(Gly‐l‐Val)(TBZ)(H2O)]·ClO4 (2) and [Cu(Gly‐l‐Val)(PBO)(H2O)]·ClO4 (3) (Gly‐l‐Val = glycyl‐l‐valine anion, HPBM = 5‐methyl‐2‐(2′‐pyridyl)benzimidazole, TBZ = 2‐(4′‐thiazolyl)benzimidazole, PBO = 2‐(2′‐pyridyl)benzoxazole), have been prepared and characterized with elemental analyses, conductivity measurements as well as various

  三种新型铜（II）配合物，[Cu（上Gly-升-Val）（HPBM）（H 2 O）]·CLO 4 ·H 2 O（1），[Cu（上Gly-升-Val）（TBZ）（ H 2 O）]·ClO 4（2）和[Cu（Glyl - Val）（PBO）（H 2 O）]·ClO 4（3）（Glyl - Val =甘氨酰l已制备了缬氨酸阴离子，HPBM = 5-甲基-2-（2'-吡啶基）苯并咪唑，TBZ = 2-（4'-噻唑基）苯并咪唑，PBO = 2-（2'-吡啶基）苯并恶唑）进行元素分析，电导率测量以及各种光谱技术。使用紫外可见光，荧光，圆二色性，热变性，粘度和对接分析方法探索了这些铜络合物与小牛胸腺DNA的相互作用。实验结果表明，所有三种复合物都可以通过插入模式与DNA结合。此外，使用MTT方法评估了细胞毒性作用，并测试了这些复合物对枯草芽孢杆菌，金黄色葡萄球菌，大肠杆菌和大肠杆菌的抗菌活性。铜绿假单胞