5-甲基-2-(3-硝基苯基)-1H-苯并咪唑 | 69570-94-1

• 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-甲基-2-(3-硝基苯基)-1H-苯并咪唑
• 中文别名: 5-甲基-2-（3-硝基苯基）-1H-苯并咪唑
• 英文名称: 5-methyl-2-(3-nitrophenyl)-1H-benzimidazole
• 英文别名: 5-methyl-2-(3-nitro-phenyl)-1(3)H-benzimidazole；5-Methyl-2-(3-nitro-phenyl)-1(3)H-benzimidazol；6-methyl-2-(3-nitrophenyl)-1H-benzimidazole
• CAS: 69570-94-1
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: PACRMTWAYUPJIE-UHFFFAOYSA-N

物化性质

• 熔点：
  121-123 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  482.8±47.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-甲基-2-(3-硝基苯基)-1H-苯并咪唑 在 10% palladium on activated carbon 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 3-(6-甲基-1H-苯并咪唑-2-基)苯胺
  参考文献：
  名称：

  Design and Synthesis of 2-Arylbenzimidazoles and Evaluation of Their Inhibitory Effect against Chlamydia pneumoniae

  摘要：

  Chlamydia pneumoniae is an intracellular bacterium that responds poorly to antibiotic treatment. Insufficient antibiotic usage leads to chronic infection, which is linked to disease processes of asthma, atherosclerosis, and Alzheimer's disease. The Chlamydia research lacks genetic tools exploited by other antimicrobial research, and thus other approaches to drug discovery must be applied. A set of 2-arylbenzimidazoles was designed based on our earlier findings, and 33 derivatives were synthesized. Derivatives were assayed against C. pneumoniae strain CWL-029 in an acute infection model using TR-FIA method at a concentration of 10 mu M, and the effects of the derivatives on the host cell viability were evaluated at the same concentration. Fourteen compounds showed at least 80% inhibition, with only minor changes in host cell viability. Nine most potential compounds were evaluated using immunofluorescence microscopy on two different strains of C. pneumoniae CWL-029 and CV-6. The N-[3-(1H-benzimidazol-2-yl)phenyl]-3-methylbenzamide (42) had minimal inhibitory concentration (MIC) of 10 mu M against CWL-029 and 6.3 mu M against the clinical strain CV-6. This study shows the high antichlamydial potential of 2-arylbenzimidazoles, which also seem to have good characteristics for lead compounds.

  DOI：

  10.1021/jm1008083
• 作为产物：
  描述：

  3-nitro-N-[2-[(3-nitrobenzoyl)amino]-4-methylphenyl]benzamide 在 对甲苯磺酸 作用下， 以 对二甲苯 为溶剂， 反应 18.0h， 以0.75 g的产率得到5-甲基-2-(3-硝基苯基)-1H-苯并咪唑
  参考文献：
  名称：

  Design and Synthesis of 2-Arylbenzimidazoles and Evaluation of Their Inhibitory Effect against Chlamydia pneumoniae

  摘要：

  Chlamydia pneumoniae is an intracellular bacterium that responds poorly to antibiotic treatment. Insufficient antibiotic usage leads to chronic infection, which is linked to disease processes of asthma, atherosclerosis, and Alzheimer's disease. The Chlamydia research lacks genetic tools exploited by other antimicrobial research, and thus other approaches to drug discovery must be applied. A set of 2-arylbenzimidazoles was designed based on our earlier findings, and 33 derivatives were synthesized. Derivatives were assayed against C. pneumoniae strain CWL-029 in an acute infection model using TR-FIA method at a concentration of 10 mu M, and the effects of the derivatives on the host cell viability were evaluated at the same concentration. Fourteen compounds showed at least 80% inhibition, with only minor changes in host cell viability. Nine most potential compounds were evaluated using immunofluorescence microscopy on two different strains of C. pneumoniae CWL-029 and CV-6. The N-[3-(1H-benzimidazol-2-yl)phenyl]-3-methylbenzamide (42) had minimal inhibitory concentration (MIC) of 10 mu M against CWL-029 and 6.3 mu M against the clinical strain CV-6. This study shows the high antichlamydial potential of 2-arylbenzimidazoles, which also seem to have good characteristics for lead compounds.

  DOI：

  10.1021/jm1008083

文献信息

• Synthesis and characterization of Cu(II) containing nanosilica triazine dendrimer: A recyclable nanocomposite material for the synthesis of benzimidazoles, benzothiazoles, bis-benzimidazoles and bis-benzothiazoles
  作者：Mahboobeh Nasr-Esfahani、Iraj Mohammadpoor-Baltork、Ahmad Reza Khosropour、Majid Moghadam、Valiollah Mirkhani、Shahram Tangestaninejad

  DOI：10.1016/j.molcata.2013.08.009

  日期：2013.11

  The present study describes the synthesis, characterization, and catalytic activity of Cu(II) containing nanosilica triazine dendrimer (Cu(II)-TD@nSiO2). The prepared catalyst was characterized by FT-IR, TGA, elemental analysis, UV–vis, FE-SEM, TEM, XPS and ICP-OES techniques. The Cu(II)-TD@nSiO2 has been used as an efficient catalyst for the preparation of various benzimidazoles, benzothiazoles, symmetrical

  本研究描述了含Cu（II）的纳米二氧化硅三嗪树枝状大分子（Cu（II）-TD @ nSiO 2）的合成，表征和催化活性。通过FT-IR，TGA，元素分析，UV-vis，FE-SEM，TEM，XPS和ICP-OES技术对制备的催化剂进行了表征。Cu（II）-TD @ nSiO 2已被用作在温和条件下制备各种苯并咪唑，苯并噻唑，对称双-苯并咪唑和双-苯并噻唑的有效催化剂。第一次，我们报告了不对称bis的合成-苯并咪唑以及同时含有苯并咪唑和苯并噻唑部分的化合物，表明该催化体系的效率。本方法提供了优异的产率，短的反应时间和简单的后处理的优点。而且，该催化剂可以容易地再循环和重复使用几次，这使得该方法具有吸引力，经济和环保。
• A Simple and Efficient One-Pot Synthesis of 2-Substituted Benzimidazoles
  作者：Kiumars Bahrami、Mohammad Khodaei、Iman Kavianinia

  DOI：10.1055/s-2007-965878

  日期：2007.2

  A simple and efficient procedure for the synthesis of substituted benzimidazoles through a one-pot condensation of o-phenylenediamines with aryl aldehydes in the presence of H2O2/HCl system in acetonitrile at room temperature is described. Short reaction time, large-scale synthesis, easy and quick isolation of the products, and excellent yields are the main advantages of this procedure.

  本文介绍了一种简单高效的一锅法合成取代苯并咪唑的工艺：在室温下，以乙腈为溶剂，在H2O2/HCl体系存在下，将邻苯二胺与芳醛进行缩合反应。该工艺的主要优点包括反应时间短、规模化合成、产物分离简便快捷以及产率优异。
• Ultrafine Pt nanoparticles supported on a dendrimer containing thiol groups: an efficient catalyst for the synthesis of benzimidazoles and benzothiazoles from benzyl alcohol derivatives in water
  作者：Zahra Zamani Nori、Amir Landarani-Isfahani、Mehrnaz Bahadori、Majid Moghadam、Valiollah Mirkhani、Shahram Tangestaninejad、Iraj Mohammadpoor-Baltork

  DOI：10.1039/d0ra06471h

  日期：——

  performance for the synthesis of benzimidazole and benzothiazole derivatives through a reaction between benzyl alcohol derivatives and 2-aminothiophenol or 1,2-phenylenediamine. No requirement for the pre-reduction of catalysts and using water as a green solvent make it an individual catalyst for these reactions. Furthermore, the catalyst can be easily recovered and reused five consecutive times in the

  基于纳米二氧化硅负载的含硫醇基团的树枝状聚合物（nSTDP）制备了新颖独特的平台，合成了超细铂纳米粒子并将其固定在nSTPD的硫醇修饰的分支上。新型催化剂 (Pt np @nSTDP) 通过 FE-SEM、TEM、ICP、XPS 和 DR UV-vis 等不同技术进行了表征。这种多相催化剂在通过苯甲醇衍生物与2-氨基苯硫酚或1,2-苯二胺反应合成苯并咪唑和苯并噻唑衍生物方面表现出优异的性能。无需预还原催化剂并使用水作为绿色溶剂，使其成为这些反应的单独催化剂。此外，该催化剂可以很容易地回收并在苯并咪唑和苯并噻唑的生产中连续重复使用五次，而没有明显的Pt浸出和活性损失，这说明了催化剂在反应过程中的化学稳定性。
• Virtual screening identification and chemical optimization of substituted 2-arylbenzimidazoles as new non-zinc-binding MMP-2 inhibitors
  作者：Antonio Laghezza、Grazia Luisi、Alessia Caradonna、Antonella Di Pizio、Luca Piemontese、Fulvio Loiodice、Mariangela Agamennone、Paolo Tortorella

  DOI：10.1016/j.bmc.2019.115257

  日期：2020.2

  structure-activity relationship (SAR) of the benzimidazole scaffold was explored by synthesis of several analogues whose inhibition activity was tested with enzyme inhibition assays. By performing the molecular simplification approach, we disclosed different sets of single-digit micromolar inhibitors of MMP-2, with up to a ten-fold increase in inhibitory activity and ameliorated selectivity towards off-target

  基质金属蛋白酶（MMPs）是锌依赖性内切蛋白酶的一大家族，已知在肿瘤的进展和侵袭性中起多种调节作用。多年来，这鼓励了针对抗癌治疗的MMP，尤其是MMP-2的方法。由于在临床上出现毒性和其他缺陷，基于（假）肽支架组装的非特异性锌结合基（ZBGs）的MMP抑制剂的早期世代已被中止，这为有或没有锌螯合剂部分的抑制剂铺平了道路。结合催化锌离子。在本文中，我们继续寻找新的非锌结合性MMP-2抑制剂：利用先前鉴定的化合物，开展了虚拟筛选（VS）运动，并导致了新一类配体的鉴定。通过合成几种类似物来探索苯并咪唑支架的构效关系（SAR），这些类似物的抑制活性已通过酶抑制试验进行了测试。通过执行分子简化方法，我们公开了不同组的MMP-2单位数微摩尔抑制剂，与所选先导化合物相比，抑制活性和对脱靶MMP-8的选择性提高了多达十倍。对具有对接的特权结构的MMP-2配合物进行的分子动力学计算证实，分析的抑制剂可避免靶
• Copper‐Mediated Diamination of Arylboronic Acids for the Synthesis of 2‐Aryl Benzimidazoles Using Trimethylsilyl Azide as the Amino Sources with Aldehydes
  作者：Zeqiang Xie、Fengtao Zhou、Ke Ding

  DOI：10.1002/adsc.202000385

  日期：2020.8.19

  A direct and versatile copper‐mediated three‐component reaction of arylboronic acids, trimethylsilyl azide and aldehydes for the synthesis of benzimidazoles is reported. The reaction is well tolerated by a wide range of substituted aromatic aldehydes and aromatic boronic acids to produce the corresponding benzimidazoles in moderate to high yields. Mechanism investigations demonstrated that copper‐promoted

  据报道，直接和通用的铜介导的三组分芳基硼酸，三甲基硅烷基叠氮化物和醛类反应可合成苯并咪唑。各种取代的芳族醛和芳族硼酸对反应具有良好的耐受性，以中等至高收率生产相应的苯并咪唑。机理研究表明，串联过程涉及铜促进的Chan-Evans-Lam偶联，CH胺化和氧化环加成反应。