5-nitro-2-pyridin-2-yl-1(3)H-benzoimidazole | 51759-60-5

• 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: 5-nitro-2-pyridin-2-yl-1(3)H-benzoimidazole
• 英文别名: 5-Nitro-2-(2-pyridinyl)-1H-benzimidazole；6-nitro-2-pyridin-2-yl-1H-benzimidazole
• CAS: 51759-60-5
• 化学式: C₁₂H₈N₄O₂
• mdl: MFCD00022691
• 分子量: 240.221
• InChiKey: VRZGTMSSHMHGPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 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：
  87.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-nitro-2-pyridin-2-yl-1(3)H-benzoimidazole 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以80%的产率得到2-(吡啶-2-基)-1H-1,3-苯并二唑-5-胺
  参考文献：
  名称：

  Metal-Mediated Inhibition of Escherichia coli Methionine Aminopeptidase:  Structure−Activity Relationships and Development of a Novel Scoring Function for Metal−Ligand Interactions

  摘要：

  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.

  DOI：

  10.1021/jm050476z
• 作为产物：
  描述：

  邻苯二胺 在 硫酸 、 硝酸 作用下， 以 硝基苯 为溶剂， 反应 2.0h， 生成 5-nitro-2-pyridin-2-yl-1(3)H-benzoimidazole
  参考文献：
  名称：

  2-取代的苯并咪唑的化学。1. 5-氨基-2-甲基（芳基，芳烷基，吡啶基）苯并咪唑

  摘要：

  DOI：

  10.1007/bf02269539

文献信息

• 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。
• Synthesis of benzoxazoles, benzothiazoles and benzimidazoles and evaluation of their antifungal, insecticidal and herbicidal activities.
  作者：TAKUZO HISANO、MASATAKA ICHIKAWA、KONOSUKE TSUMOTO、MASANOBU TASAKI

  DOI：10.1248/cpb.30.2996

  日期：——

  Benzoxazoles, benzothiazoles and benzimidazoles having substituents on the azole and benzene nuclei were synthesized evaluated for antifungal, insecticidal and herbicidal activities. It was found that benzimidazoles tended to exhibit antifungal activity while benzothiazoles tended to show herbicidal activity. Chloro, trifluoromethyl, methoxy and ethoxy groups at the 5 position were potent substituents, and the 2-pyridyl group at the 2 position is a common structural unit. Among several active derivatives, 7-chloro-2-(2-pyridyl) benzimidazole and 2-(2-pyridyl)-5-trifluoromethylbenzothiazole exhibited significant activity against Panonycus citri.

  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。
• Teststreifen zum Nachweis von Leukozyten im Harn
  申请人：MACHEREY-NAGEL & Co, Chemikalienhandel

  公开号：EP0120396A2

  公开（公告）日：1984-10-03

  Die Erfindung betrifft die Verwendung einer Verbindung der chemischen Formel worin R, und R2 gleich oder verschieden sind und Wasserstoff, Halogen, eine niedere Alkyl- oder Alkoxygruppe mit 1 bis 4 C-Atomen, eine (C1-C4)-Dialkylamino-. eine Acetylaminogruppe, eine Nitrogruppe oder einen gegebenenfalls substituierten oder annelierten Aromaten bedeuten, n eine ganze Zahl von 1 bis 4, bevorzugt 1 bis 2, und m ebenfalls eine ganze Zahl von 1 bis 4, bevorzugt 1 bis 2 ist, und R3 für Wasserstoff, eine niedere Alkylgruppe mit 1 bis 4, bevorzugt 1 bis 2 C-Atomen, einen niederen Acyl-, bevorzugt den Acetylrest, oder einen Cyanoalkylrest, bevorzugt den Cyanoethylrest, steht oder eines Salzes dieser Verbindung in einem Mittel, insbesondere zum Nachweis von Leukozyten und anderen esterolytisch und/oder proteolytisch wirksamen Substanzen in Körperflüssigkeiten und Ausscheidungen, insbesondere auf einem saugfähigen Träger zusammen mit einem enzymspezifischen Substrat und/oder Chromogen sowie weiteren Hilfsmitteln wie einem Puffersystem, ggfs. Verdickungsmitteln, oberflächenaktiven Mitteln, Oxidationsmitteln und/oder Stabilisatoren.

  本发明涉及一种化学式为 其中 R 和 R2 相同或不同，并且是氢、卤素、具有 1 至 4 个碳原子的低级烷基或烷氧基、(C1-C4)-二烷基氨基、乙酰氨基、硝基或任选取代或融合的芳香族化合物、 n 是 1 至 4 的整数，最好是 1 至 2，以及 m 也是 1 至 4 的整数，最好是 1 至 2，以及 R3 是氢、具有 1 至 4 个碳原子（最好是 1 至 2 个）的低级烷基、低级酰基（最好是乙酰基）或氰烷基（最好是氰乙基）或该化合物的盐 在制剂中，特别是用于检测体液和排泄物中的白细胞和其他酯溶活性物质和/或蛋白溶活性物质，尤其是在吸收载体上，与酶特异性底物和/或显色剂及进一步的辅助剂如缓冲体系、可能的增稠剂、表面活性剂、氧化剂和/或稳定剂一起使用。
• Benzimidazole derivatives: synthesis, leishmanicidal effectiveness, and molecular docking studies
  作者：Awais Shaukat、Hira M. Mirza、Amna H. Ansari、Masoom Yasinzai、Sohail Z. Zaidi、Sana Dilshad、Farzana L. Ansari

  DOI：10.1007/s00044-012-0375-5

  日期：2013.8

  Leishmanolysin GP63 is a zinc metalloprotease, expressed at the surface of Leishmania promastigotes. Studies on this protein are hindered as only a limited number of effective non-toxic inhibitors of this drug target are known. Present study describes the identification of a variety of 2-aryl- and 5-nitro-2-arylbenzimidazoles as new GP63 inhibitors. All the compounds were tested for in vitro activity against the promastigote form of Leishmania major and showed very good activity. 2-(Thiophen-2-yl)-1H-benzimidazole (19) and 2-(1H-indol-3-yl)-5-nitro-1H-benzimidazole (34) with IC50 value of 0.62 mu g/mL were identified as lead of this library. Molecular docking studies were performed on binding site of GP63 to study the binding mode of compounds. The results of both in vitro and in silico studies clearly indicated that benzimidazoles may serve as new drug candidates in the combat against leishmaniasis.
• Ichikawa, Masataka; Yamamoto, Chiyuki; Hisano, Takuzo, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 10, p. 3042 - 3047
  作者：Ichikawa, Masataka、Yamamoto, Chiyuki、Hisano, Takuzo

  DOI：——

  日期：——