5-硝基-2-(4-吡啶基)-1H-苯并咪唑 | 148533-73-7

• 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: 5-硝基-2-(4-吡啶基)-1H-苯并咪唑
• 中文别名: 5-硝基-2-(吡啶-4-基)-1H-苯并[D]咪唑
• 英文名称: 5-nitro-2-(4-pyridyl)-1H-benzimidazole
• 英文别名: 5-nitro-2-(pyridin-4-yl)-1H-benzo[d]imidazole；5-nitro-2-(pyridine-4-yl)-1H-benzo[d]imidazole；5-Nitro-2-(4-pyridinyl)-1H-benzimidazole；6-nitro-2-pyridin-4-yl-1H-benzimidazole
• CAS: 148533-73-7
• 化学式: C₁₂H₈N₄O₂
• mdl: MFCD00447068
• 分子量: 240.221
• InChiKey: MPOIUZUPKNLRIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  224-226 °C
• 沸点：
  527.1±56.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)
• 溶解度：
  8 [ug/mL]

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

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-硝基-2-(4-吡啶基)-1H-苯并咪唑 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.5h， 生成 2-phenoxy-N-((2-pyridin-4-yl)-1H-benzo[d]imidazole-5-yl)propanamide
  参考文献：
  名称：

  基于苯并恶唑的隐孢子虫肌苷5'-单磷酸脱氢酶抑制剂的优化

  摘要：

  Cryptosporidium parvum是一种肠道原生动物寄生虫，已成为导致腹泻、营养不良和肠胃炎的主要原因，并构成潜在的生物恐怖主义威胁。C. parvum通过依赖肌苷 5'-单磷酸脱氢酶 (IMPDH) 的简化途径从宿主腺苷合成鸟嘌呤核苷酸。我们之前已经通过高通量筛选确定了几种寄生虫选择性C. parvum IMPDH ( Cp IMPDH) 抑制剂。在本文中，我们报告了一系列苯并恶唑衍生物的构效关系 (SAR)，其中许多化合物证明了Cp IMPDH IC 50纳摩尔范围内的值和比人 IMPDH (hIMPDH) 高 500 倍的选择性。与之前报道的Cp IMPDH 抑制剂不同，这些化合物是对 NAD + 的竞争性抑制剂。SAR 研究表明，在苯并恶唑的 2 位需要吡啶和其他小的杂芳族取代基才能产生有效的抑制活性。此外，还强调了关于苯并恶唑和抑制剂的酰胺部分的其他几个 SAR 结论，包括优选的立体化学。还介绍了代表性

  DOI：

  10.1021/jm400241j
• 作为产物：
  描述：

  2-(4-吡啶)苯并咪唑 在 硫酸 、 硝酸 作用下， 以84%的产率得到5-硝基-2-(4-吡啶基)-1H-苯并咪唑
  参考文献：
  名称：

  杂环甜菜。二十二。4-硝基苯并咪唑啉（偶氮）内盐及其衍生物，带有多个环形间隔基。合成，表征和抗滴虫活性。

  摘要：

  探索了吡啶鎓（咪唑鎓）4-硝基苯并咪唑酸酯甜菜碱及其衍生物与几个环间键合的合成。它们的抗原生动物活性也已被检查。

  DOI：

  10.1248/cpb.43.493

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。
• Heterocyclic Betaines. XXII. Azinium(Azolium)4-Nitrobenzimidazolate Inner Salts and Their Derivatives with Several Interannular Spacers. Synthesis, Characterization and Antitrichomonal Activity.
  作者：Ermitas ALCALDE、Lluisa PEREZ-GARCIA、Immaculada DINARES、Jordi FRIGOLA

  DOI：10.1248/cpb.43.493

  日期：——

  The synthesis of an ensemble of pyridinium(imidazolium) 4-nitrobenzimidazolate betaines and their derivatives with several interannular linkages has been explored. Their antiprotozoal activity has also been examined.

  探索了吡啶鎓（咪唑鎓）4-硝基苯并咪唑酸酯甜菜碱及其衍生物与几个环间键合的合成。它们的抗原生动物活性也已被检查。
• COMPOUNDS AND METHODS FOR TREATING MAMMALIAN GASTROINTESTINAL MICROBIAL INFECTIONS
  申请人：Brandeis University

  公开号：US20150210727A1

  公开（公告）日：2015-07-30

  Disclosed are compounds and pharmaceutically acceptable salts thereof, which are useful as inhibitors of IMPDH. In certain embodiments, a compound selectively inhibits a parasitic IMPDH versus a host IMPDH. Also disclosed are pharmaceutical compositions comprising one or more compounds of the invention. Related methods of treating various parasitic and bacterial infections in mammals are disclosed. Moreover, the compounds may be used alone or in combination with other therapeutic or prophylactic agents, such as anti-virals, anti-inflammatory agents, antimicrobials and immunosuppressants.

  本发明公开了一种化合物及其药学上可接受的盐，它们可用作IMPDH的抑制剂。在某些实施例中，该化合物选择性地抑制寄生IMPDH而不影响宿主IMPDH。本发明还公开了包含本发明中一种或多种化合物的制药组合物。公开了治疗哺乳动物中各种寄生虫和细菌感染的相关方法。此外，这些化合物可单独或与其他治疗或预防药物，如抗病毒药物、抗炎药物、抗微生物药物和免疫抑制剂一起使用。
• Benzoimidazole derivatives as anticancer agents
  申请人：CENTRE LEON BERARD

  公开号：US11384081B2

  公开（公告）日：2022-07-12

  The disclosure relates to benzoimidazole derivatives, acting as anticancer drugs, as well as pharmaceutical composition containing said compounds. These compounds are able to firstly inhibit the protein/protein interactions of the MAP Kinase Erk, leading to inhibition of proliferation and secondly to induce apoptosis in human cancer cell lines.

  本公开涉及作为抗癌药物的苯并咪唑衍生物，以及含有上述化合物的药物组合物。这些化合物首先能抑制 MAP 激酶 Erk 的蛋白/蛋白相互作用，从而抑制增殖，其次能诱导人类癌细胞株凋亡。
• Synthesis and evaluation of novel bacterial rRNA-binding benzimidazoles by mass spectrometry
  作者：Yun He、Jun Yang、Baogen Wu、Dale Robinson、Kelly Sprankle、Pei-Pei Kung、Kristin Lowery、V. Mohan、Steve Hofstadler、Eric E. Swayze、Rich Griffey

  DOI：10.1016/j.bmcl.2003.11.031

  日期：2004.2

  A series of novel benzimidazoles were efficiently synthesized using both solution- and solid-phase chemistry. These compounds were found to bind to the bacterial 16S ribosomal RNA A-site with micromolar affinities using unique mass spectrometry-based assays. (C) 2003 Elsevier Ltd. All rights reserved.