6-氯-2-吡啶-2-基-1H-苯并咪唑 | 63053-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 6-氯-2-吡啶-2-基-1H-苯并咪唑
• 英文名称: 5-chloro-2-(2-pyridyl)benzimidazole
• 英文别名: 5-chloro-2-(pyridin-2-yl)-1H-benzo[d]imidazole；6-chloro-2-(pyridin-2-yl)-1H-1,3-benzodiazole；6-chloro-2-pyridin-2-yl-1H-benzimidazole
• CAS: 63053-15-6
• 化学式: C₁₂H₈ClN₃
• mdl: MFCD11226373
• 分子量: 229.669
• InChiKey: AIASBFLKLNIZOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙烯基吡啶 、 6-氯-2-吡啶-2-基-1H-苯并咪唑 在 溶剂黄146 作用下， 反应 6.0h， 以82%的产率得到5-氯-2-吡啶-2-基-1-(2-吡啶-2-基乙基)苯并咪唑
  参考文献：
  名称：

  Synthesis of benzoxazoles, benzothiazoles and benzimidazoles and evaluation of their antifungal, insecticidal and herbicidal activities.

  摘要：

  合成了在偶氮和苯环上具有取代基的苯并噁唑、苯并噻唑和苯并咪唑，并评估其抗真菌、杀虫和除草活性。研究发现，苯并咪唑倾向于表现出抗真菌活性，而苯并噻唑则倾向于显示除草活性。在5位位置上的氯、三氟甲基、甲氧基和乙氧基基团是有效的取代基，而在2位位置的吡啶基是一个常见的结构单元。在几种具有活性的衍生物中，7-氯-2-(2-吡啶基)苯并咪唑和2-(2-吡啶基)-5-三氟甲基苯并噻唑对柑橘红蜘蛛表现出显著活性。

  DOI：

  10.1248/cpb.30.2996
• 作为产物：
  描述：

  5-Chloro-2-pyridin-2-yl-1-(2-pyridin-4-yl-ethyl)-1H-benzoimidazole 在 三氯化铝 作用下， 以 various solvent(s) 为溶剂， 反应 0.5h， 生成 6-氯-2-吡啶-2-基-1H-苯并咪唑
  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

• 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。
• Synthesis of Pyridinyl-benzo[d]imidazole/Pyridinyl-benzo[d]thiazole Derivatives and their Yeast Glucose Uptake Activity In Vitro
  作者：Momin Khan、Riaz Ahmad、Gauhar Rehman、Naeem Gul、Sana Shah、Uzma Salar、Shahnaz Perveen、Khalid Mohammed Khan

  DOI：10.2174/1570180815666181004102209

  日期：2019.9.11

  Diabetes is the primary cause of fatality and disability all over the world, in recent past, we have reported various classes of compounds as anti-glycating agents and we have also reported benzimidazole and benzothiazole derivatives as a potential class of anti-glycating agents. This encouraged us to evaluate the pyridinyl benzimidazole/pyridinyl benzothiazole derivatives 1-27 for yeast glucose uptake activity.

  In the present study, an equimolar mixture of pyridine carboxaldehyde derivatives (1 mmol) and sodium metabisulphite (1 mmol) in DMF (10 mL) was stirred for 10 to 15 min, followed by addition of o-phenylene diamine/2-aminothiophenol (1 mmol) into it and refluxed for 3 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was poured into crushed ice. Precipitates were formed which were collected by filtration to produce compounds 1-27 in good yields. Recrystallization from methanol yielded pure crystals.

  Our present study showed that all compounds showed a varying degree of yeast glucose uptake activity in the range IC50 = 36.43-272.20 µM, compared to standard metronidazole (IC50 = 41.86 ± 0.09 µM). Compounds 5 (IC50 = 38.14 ± 0.17 µM), 6 (IC50 = 40.23 ± 0.20 µM), and 7 (IC50 = 36.43 ± 0.02 µM) showed an excellent yeast glucose uptake activity better than the standard.

  Pyridinyl benzimidazole/pyridinyl benzothiazole derivatives 1-27 were synthesized, structurally characterized, and evaluated for in vitro yeast glucose uptake activity. Compounds 5 (IC50 = 38.14 ± 0.17 µM), 6 (IC50 = 40.23 ± 0.20 µM), and 7 (IC50 = 36.43 ± 0.02 µM) demonstrated potent yeast glucose uptake activity as compared to standard metronidazole (IC50 = 41.86 ± 0.09 µM). This study identified a number of potential lead molecules which can be helpful in lowering the blood glucose level in hyperglycemia.

  背景：糖尿病是全球致死和致残的主要原因，最近，我们已报告各种类别的化合物作为抗糖基化剂，并且我们还报告苯并咪唑和苯并噻唑衍生物作为一种潜在的抗糖基化剂类。这激励我们评估吡啶基苯并咪唑/吡啶基苯并噻唑衍生物1-27对酵母葡萄糖摄取活性的作用。 方法：在本研究中，将吡啶羧醛衍生物（1 mmol）和亚硫酸钠（1 mmol）在DMF（10 mL）中等摩尔混合物搅拌10至15分钟，然后加入邻苯二胺/2-氨基硫酚（1 mmol）并回流3小时。通过薄层色谱监测反应进展。反应完成后，将反应混合物倒入碎冰中。形成沉淀，通过过滤收集，产生产率良好的化合物1-27。用甲醇再结晶得到纯晶体。 结果：我们的研究表明，所有化合物在酵母葡萄糖摄取活性范围内显示出不同程度的活性，IC50 = 36.43-272.20 µM，与标准甲硝唑（IC50 = 41.86 ± 0.09 µM）相比。化合物5（IC50 = 38.14 ± 0.17 µM）、6（IC50 = 40.23 ± 0.20 µM）和7（IC50 = 36.43 ± 0.02 µM）显示出优异的酵母葡萄糖摄取活性，优于标准物质。 结论：合成了吡啶基苯并咪唑/吡啶基苯并噻唑衍生物1-27，进行了结构表征，并评估了体外酵母葡萄糖摄取活性。化合物5（IC50 = 38.14 ± 0.17 µM）、6（IC50 = 40.23 ± 0.20 µM）和7（IC50 = 36.43 ± 0.02 µM）表现出强大的酵母葡萄糖摄取活性，与标准甲硝唑（IC50 = 41.86 ± 0.09 µM）相比。该研究确定了一系列潜在的先导分子，有助于降低高血糖水平。
• Amphiphilic Dendrimer as Reverse Micelle: Synthesis, Characterization and Application as Homogeneous Organocatalyst
  作者：P.B. Sherly mole、Smitha George、A.M. Shebitha、V. Kannan、Suseela Mathew、K.K. Asha、K. Sreekumar

  DOI：10.1016/j.tet.2019.130676

  日期：2019.11

  synthesizing various aryl and heteroaryl 2-substituted benzimidazoles. The synthesized dendritic organocatalyst was proved to be amazingly reactive and gave high yield of products within a few minutes at room temperature with low catalyst loading. Here, a new stable hemiaminal, the species rarely been detected and much less isolated in bulk, was obtained during the synthesis of benzimidazoles. Moreover, this

  核心和表面末端基团是树枝状聚合物中的两个主要催化位点。在大多数报道的实施例中，树状催化中的催化位点是表面末端官能团。该透视文章涉及基于树枝状聚合物的催化，涉及这两个催化位点和树枝状聚合物腔。内部空腔通过产生反胶束状外观来催化而提供了纳米级反应器位点。为了探索该领域的重要成就，合成了具有两亲性质的低代PAMAM树枝状聚合物，该聚合物具有带有大量侧链氨基的聚合物核，并浓缩了其​​催化活性。通过合成各种芳基和杂芳基2-取代的苯并咪唑突出了有关正和/或负催化活性的关键特征。已证明合成的树枝状有机催化剂具有惊人的反应性，并在室温下几分钟内以低催化剂负载量提供了高收率的产品。在此，在合成苯并咪唑的过程中，获得了一种新的稳定的血红素，很少检测到该物种，而散装的则很少。此外，这是首次报道的使用均相PAMAM树枝状大分子作为碱性有机催化剂合成苯并咪唑的方法。在合成苯并咪唑的过程中，几乎没有发现这种物种，而且
• Benzimidazolic complexes of methyltrioxorhenium(VII): Synthesis and application in catalytic olefin epoxidation
  作者：Su Li、Bo Zhang、Fritz. E. Kühn

  DOI：10.1016/j.jorganchem.2012.11.006

  日期：2013.4

  characterized by IR, 1H, 13C NMR, MS and elemental analysis as well as tested as catalysts for olefin epoxidation using 35% aqueous hydrogen peroxide as oxidant under mild condition. The influence of different ligand concentrations was also examined. The results show that the complexes are highly selective in olefin epoxidation and good yields can be obtained when excess ligand is applied.

  七个新的通式为CH 3 ReO 3 ·L的甲基三氧杂（（VII）（MTO）的路易斯碱加合物（L =二齿苯并咪唑基配体，即（L = 2-（2-吡啶基）-1H-苯并咪唑，5-甲基- 2-（2-吡啶基）苯并咪唑，5-氯-2-（2-吡啶基）苯并咪唑，2-（2-吡啶基）-1H-咪唑-[4,5-b]-吡啶，2-（2-喹啉）制备苯并咪唑，2-（5-甲基-1H-苯并咪唑-2-基）-喹啉和2-（5-氯-1H-苯并咪唑-2-基）-喹啉））。所有配合物的特征在于IR，1 H，1313 C NMR，MS和元素分析，以及在温和条件下使用35％的过氧化氢水溶液作为氧化剂的烯烃环氧化催化剂，均经过测试。还检查了不同配体浓度的影响。结果表明，该配合物在烯烃环氧化中具有高选择性，并且当使用过量的配体时可以获得良好的产率。
• Synthesis, DNA binding, antibacterial and anticancer properties of two novel water-soluble copper(II) complexes containing gluconate
  作者：Dai-Hong Cai、Chun-Lian Zhang、Qi-Yan Liu、Liang He、Yun-Jun Liu、Ya-Hong Xiong、Xue-Yi Le

  DOI：10.1016/j.ejmech.2021.113182

  日期：2021.3

  that both complexes had good inhibitory activity against three Gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis, Listeria monocytogenes) and one Gram-negative bacterium (Escherichia coli) and good cytotoxic activity toward the tested cancer cells (A549, HeLa and SGC-7901). CuG2 showed higher antimicrobial and cytotoxic activities than CuG1, which was consistent with their binding strength

  本文研究了两种新的Cu（II）配合物，[Cu（Gluc）（HPB）（H 2 O）] Gluc（CuG1）和[Cu（Gluc）（HPBC）（H 2 O）] Gluc（CuG2）（其中HPB = 2-（2'-吡啶基）苯并咪唑，HPBC = 5-氯-2-（2'-吡啶基）苯并咪唑，Gluc =  d-葡萄糖酸），具有良好的水溶性合成和表征。这些配合物表现出五配位的四角锥几何形状。使用多光谱，粘度测量，分子对接和凝胶电泳分析方法研究了复合物的DNA结合和切割特性。结果表明，在抗坏血酸存在下，复合物可通过插入和凹槽结合与DNA相互作用，并通过单线态氧依赖性途径裂解CT-DNA。对体外抗菌和抗癌活性的研究表明，两种复合物均对三种革兰氏阳性细菌（金黄色葡萄球菌，枯草芽孢杆菌，单核细胞增生性李斯特菌（Listeria monocytogenes）和一种革兰氏阴性细菌（Escherichia coli）对被测