1H-Benzimidazole, 2,2'-(1,2-ethanediyl)bis[5-nitro- | 5887-57-0

• 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: 1H-Benzimidazole, 2,2'-(1,2-ethanediyl)bis[5-nitro-
• 英文别名: 6-nitro-2-[2-(6-nitro-1H-benzimidazol-2-yl)ethyl]-1H-benzimidazole
• CAS: 5887-57-0
• 化学式: C₁₆H₁₂N₆O₄
• mdl: MFCD00371985
• 分子量: 352.309
• InChiKey: BOXGNPCIGUQGGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1H-Benzimidazole, 2,2'-(1,2-ethanediyl)bis[5-nitro- 在 palladium on activated charcoal 氢气 作用下， 以 水 、 三氟乙酸 为溶剂， 反应 1.0h， 生成 1,2-bis(5-amino-2-benzimidazolyl)ethane
  参考文献：
  名称：

  烷基和芳基连接的双（ami基苯并咪唑）和双（ami基吲哚）的结构，DNA小沟结合和碱基对特异性。

  摘要：

  已经制备了一系列具有变化的连接链的双（ami基苯并咪唑）和双（ami基吲哚），所述连接链连接芳族基团并且对碱性a基进行了各种修饰。小牛胸腺（CT）DNA和核酸均聚物[poly（dA）.poly（dT），poly（dA-dT）.poly-（dA-dT）和poly（dG-dC）.poly（dG-dC） ）]已经通过热变性（ΔTm）和粘度研究了这些化合物的结合性能。该化合物对poly（dA）.poly（dT）和poly（dA-dT）.poly（dA-dT）的亲和力大于对poly（dG-dC）.poly（dG-dC）的亲和力。粘度滴定表明该化合物不通过嵌入结合。分子模型研究和生物物理数据表明，分子与CT DNA和均聚物的小沟结合。分子形状的分析与这种核酸结合模式一致。与苯并咪唑环相连的亚甲基数量为偶数的化合物比亚甲基数量为奇数的化合物对DNA的亲和力更高。确定分子中四个定义的基团的曲率半径的分子模

  DOI：

  10.1021/jm00064a008
• 作为产物：
  描述：

  1,2-bis(2-benzimidazolyl)ethane 在 硫酸 、 potassium nitrate 作用下， 生成 1H-Benzimidazole, 2,2'-(1,2-ethanediyl)bis[5-nitro-
  参考文献：
  名称：

  Feitelson et al., Journal of the Chemical Society, 1952, p. 2389,2393

  摘要：

  DOI：

文献信息

• Bisbenzimidazole Derivatives as Potential Antimicrobial Agents: Design, Synthesis, Biological Evaluation and Pharmacophore Analysis
  作者：Ronak Haj Ersan、Kayhan Bolelli、Serpil Gonca、Aylin Dogen、Serdar Burmaoglu、Oztekin Algul

  DOI：10.1007/s11094-021-02389-x

  日期：2021.5

  In an attempt to design and synthesize a potent class of antimicrobials, 1,2-phenylenediamine derivatives were reacted with various aliphatic and heteroaliphatic dicarboxylic acids to generate a small library of 26 head-to-head bisbenzimidazole compounds (16 – 42) using the polyphosphoric acid method. These compounds were screened for their antibacterial activity and their antifungal activity. Compound 25 showed maximum potency against both Gram-positive and Gram-negative bacterial strains with minimum inhibitory concentration (MIC) values in the range of 7.81 – 31.25 μg/mL. In particular, it showed the maximum MIC values of 7.81 μg/mL against Gram-negative bacteria, which was four-fold more active than the standard drug ampicillin (MIC = 32.25 μg/mL). Compound 19 was found to be the most active against S. aureus with a MIC value of < 3.90 μg/mL, whereas the remaining compounds showed only low-to-moderate activity. Furthermore, all compounds exhibited low activity against all fungal strains in comparison to the standard drug fluconazole. I addition, pharmacophore hypotheses were generated to analyze structure–activity relationships between the molecular structures and antimicrobial activities on E. coli. This pharmacophore model can be useful in order to design new antimicrobial drugs. It can be suggested that the substitution of a phenyl ring at the 5/6 and 5′/6′ positions in symmetric bisbenzimidazole derivatives produces compounds with promising antimicrobial activity.

  为了设计并合成一类高效的抗菌药物，我们通过多磷酸法，将1,2-苯二胺衍生物与各种脂肪族和杂脂肪族二羧酸反应，生成了一个包含26个头对头双苯并咪唑化合物（16 – 42）的小型库。这些化合物经过筛选，评估了它们的抗菌活性和抗真菌活性。化合物25对革兰氏阳性和革兰氏阴性细菌株显示出最高的活性，其最低抑制浓度（MIC）值在7.81至31.25 μg/mL范围内。特别是，它对革兰氏阴性细菌显示出最高的MIC值7.81 μg/mL，比标准药物氨苄西林（MIC = 32.25 μg/mL）高出四倍。化合物19对金黄色葡萄球菌显示出最高的活性，其MIC值小于3.90 μg/mL，而其他化合物仅显示出低至中等的活性。此外，与标准药物氟康唑相比，所有化合物对所有真菌株均显示出低活性。此外，生成了药效团假设，以分析大肠杆菌上的分子结构与抗菌活性之间的结构-活性关系。这个药效团模型对于设计新的抗菌药物可能非常有用。可以建议，在对称双苯并咪唑衍生物的5/6和5′/6′位置上取代苯环会产生具有有前景的抗菌活性的化合物。
• Preparation and characterization of new soluble benzimidazole–imide copolymers
  作者：M. Berrada、F. Carriere、Y. Abboud、A. Abourriche、A. Benamara、N. Lajrhed、M. Kabbaj、M. Berrada

  DOI：10.1039/b205150h

  日期：——

  The present necessity to use heat-resistant materials in electronics justifies the scientific interest in different heterocyclic polymers. This paper is especially concerned with the preparation of novel heat-resistant polyimides having bisbenzimidazole moieties in the main chain and their applications as dielectric films. A soluble copolyimide was prepared by a two-step synthesis from aromatic dianhydrides and aromatic diamines. The bisbenzimidazole diamine was prepared by reduction of the corresponding dinitro compound. The diamine was reacted with various aromatic dianhydrides to prepare a series of alternating benzimidazole–imide copolymers via the poly(amic acid) precursors and thermal or chemical imidization. Monomers and polymers were characterized by conventional methods and their physical properties such as solution viscosity, solubility properties, thermal stability and thermal behaviour were studied. All copolymers were obtained in high yields having inherent viscosities ηinh that ranged from 0.60 to 0.98 dL g−1. Thin films of the copolymer were tough and flexible, having tensile strengths as high as 100 MPa. Glass transition temperatures were observed between 275 and 328 °C. Thermogravimetric analyses indicated that the thermal degradation of poly(benzimidazole–imide) occurs around 530 °C, which is ca. 80 °C higher than polyimide, confirming that the introduction of the bisbenzimidazole component improved the thermal stability of polyimide.

  目前电子领域对耐热材料的需求使得不同的杂环聚合物引起了科学界的关注。本文特别关注含有双苯并咪唑基团的新型耐热聚酰亚胺的制备及其作为绝缘薄膜的应用。通过对芳香二酐和芳香二胺的两步合成，制备了一种可溶性共聚酰亚胺。双苯并咪唑二胺是通过还原相应的二硝基化合物制备的。该二胺与多种芳香二酐反应，通过聚（酰胺酸）前驱体及热或化学酰亚胺化反应制备出一系列交替的苯并咪唑-酰亚胺共聚物。单体和聚合物通过常规方法进行了表征，并研究了其物理性质，如溶液粘度、溶解特性、热稳定性和热行为。所有共聚物都以高产率获得，固有粘度ηinh范围为0.60至0.98 dL g⁻¹。共聚物的薄膜坚韧且柔韧，拉伸强度高达100 MPa。玻璃转变温度在275至328°C之间。热重分析表明，聚（苯并咪唑-酰亚胺）的热降解发生在约530°C，这比聚酰亚胺高出约80°C，确认了双苯并咪唑组分的引入提高了聚酰亚胺的热稳定性。
• Efficient and Practical Procedures for the Synthesis of Bis-benzimidazoles in Dry Media under Various Reaction Conditions
  作者：Kioumars Aghapoor、Farshid Mohsenzadeh、Hossein Reza Darabi

  DOI：10.1515/znb-2005-0814

  日期：2005.8.1

  Some different approaches have been developed in order to determine the most efficient preparation of bis-benzimidazoles 1a - f under solvent-free conditions. All of the selected methods are simple, avoiding heating with corrosive mineral acids. Heating of the reactants on a sand bath method appears to have higher efficiency.

  为了确定在无溶剂条件下双苯并咪唑 1a-f 的最有效制备，已经开发了一些不同的方法。所有选择的方法都很简单，避免用腐蚀性矿物酸加热。用砂浴法加热反应物似乎具有更高的效率。
• Self-assembly of a [2]pseudorotaxane complex by the threading of a nitrobenzimidazol-based guest on dibenzo-24-crown ether host
  作者：Dolores Castillo、Ruy Cervantes、Carlos Frontana、Felipe J. Gonzalez、Jorge Tiburcio

  DOI：10.1002/poc.3321

  日期：2014.8

  dibenzo‐24‐crown‐8 ether host (DB24C8) giving rise to a [2]pseudorotaxane complex [1H2⊂DB24C8]2+, regardless of the counterion, [CF3SO3]− or [CF3COO] −. The interpenetrated structure of [1H2⊂DB24C8]2+ was proven by solution NMR and X‐ray crystallography. This host–guest complex is held together by several non‐covalent interactions, such as hydrogen bonding and ion‐dipole. An electrochemical study of [1H2]2+ in the

  在微波辐射下合成了先前报道的1,2-双（苯并咪唑-2-基）乙烷基序的新衍生物阳离子[1H 2 ] 2+，并通过溶液NMR，高分辨率质谱，循环伏安法进行了全面表征和X射线晶体学。该阳离子呈线性几何形状，并结合了硝基取代基作为电化学处理方法。在溶液中，阳离子[1H 2 ] 2+，能够螺纹二苯并-24-冠-8醚宿主的特性（DB24C8）便出现了[2]准轮烷络合物[1H空腔2 ⊂DB24C8] 2+不管，抗衡离子[CF 3 SO 3 ] -或[CF 3 COO]-。的互穿结构[1H 2 ⊂DB24C8] 2+通过溶液NMR和X-射线晶体学证实。该主客体复合物通过几种非共价相互作用而结合在一起，例如氢键和离子偶极子。在存在可变量的DB24C8的情况下进行[1H 2 ] 2+的电化学研究；由于阳离子[1H 2 ] 2+的不可逆氧化还原行为，因此无法通过电化学方式控制DB24C8的缔合/解离过程。版权所有©2014
• Komai et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 242
  作者：Komai et al.

  DOI：——

  日期：——