2-(((1H-benzo[d]imidazol-2-yl)methyl)-thio)-1H-benzo[d]imidazole | 137856-21-4

• 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: 2-(((1H-benzo[d]imidazol-2-yl)methyl)-thio)-1H-benzo[d]imidazole
• 英文别名: 1H-Benzimidazol-2-yl 1H-benzimidazol-2-ylmethyl sulfide；2-(1H-benzimidazol-2-ylmethylsulfanyl)-1H-benzimidazole
• CAS: 137856-21-4
• 化学式: C₁₅H₁₂N₄S
• mdl: MFCD00423485
• 分子量: 280.353
• InChiKey: ONMJBLRZULUDFX-UHFFFAOYSA-N

物化性质

• 熔点：
  255 °C
• 沸点：
  610.0±57.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  82.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(((1H-benzo[d]imidazol-2-yl)methyl)-thio)-1H-benzo[d]imidazole 、 zinc(II) chloride 以 甲醇 为溶剂， 以80%的产率得到Zn(2-((1H-benzo[d]imidazol-2-yl)methylthio)-1H-benzo[d]imidazole)Cl₂
  参考文献：
  名称：

  Synthesis, X-ray structure, theoretical investigation, corrosion inhibition and antimicrobial activity of benzimidazole thioether and theirs metal complexes

  摘要：

  Synthesis, characterization, corrosion inhibition as well as antimicrobial activity of the coordination compounds {Co(bbms)Cl-2}, {Zn(bbms)Cl-2}, {Co(btmb)Cl-2) and {Zn(btmb)Cl-2} containing benzimidazole thioether have been described. Co(bbms) and Zn(bbms) as well as Co(btmb) and Zn(btmb) are isostructural with space group Pbca and P21 respectively.The coordination polyhedron around the metal center for all complexes may be described as a quasi regular tetragonal geometry. The corrosion inhibition study of these complexes for steel in 0.5 M H2SO4 medium has been investigated using potentiodynamic polarization and EIS techniques. These later show the corrosion inhibition ability of the prepared complexes for steel in acid medium. A new procedure has been developed for antimicrobial assay using a solid tablet of the corresponding complexes: These later show moderate to significant antimicrobial activities against: Pseudomonas syringae, Staphylococcus aureus and Pichia caribbica. DFT/BP86 calculations have been carried out on the neutral complexes and on the monoanionic of (1) and (3) forms of singlet and triplet species. The optimized structures reproduce those observed experimentally, while the reduced ones undergo remarkable geometrical parameters variations. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2016.08.045
• 作为产物：
  描述：

  1H-苯并咪唑-2-硫醇 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 21.0h， 生成 2-(((1H-benzo[d]imidazol-2-yl)methyl)-thio)-1H-benzo[d]imidazole
  参考文献：
  名称：

  头对头双苯并唑衍生物作为抗增殖剂：设计、合成、体外活性和 SAR 分析。

  摘要：

  摘要 在目前的工作中，设计并合成了一系列双苯并唑衍生物作为抗增殖剂。使用 MTT 法研究这些化合物的抗增殖活性。双苯并唑衍生物对所有四种测试的癌细胞系均显示出显着的抗增殖活性。在各种双苯并唑衍生物中，双苯并恶唑衍生物表现出最有希望的抗癌活性，其次是双苯并咪唑和双苯并噻唑衍生物。与甲氨蝶呤（阳性对照）相比，所有衍生物在正常人细胞中的毒性较低，表明这些双苯并唑衍生物具有选择性和有效的抗增殖活性。详细分析了双苯并唑衍生物中存在的杂芳族系统和接头的构效关系。计算机 ADMET 预测显示，双苯并唑是一种药物样小分子，具有良好的安全性。化合物31是一种潜在的抗增殖打击化合物，具有不同于甲氨蝶呤的独特细胞毒活性。 图形摘要 已设计合成了 21 种双苯并恶唑衍生物，并对其进行了评估，这些衍生物对四种人类肿瘤细胞系具有抗增殖活性。

  DOI：

  10.1007/s11030-020-10115-0

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。
• Synthesis and Antibacterial Evaluation of Some Novel Imidazole and Benzimidazole Sulfonamides
  作者：Nassir Al-Mohammed、Yatimah Alias、Zanariah Abdullah、Raied Shakir、Ekhlass Taha、Aidil Hamid

  DOI：10.3390/molecules181011978

  日期：——

  Several new substituted sulfonamide compounds were synthesized and their structures were confirmed by 1H-NMR, 13C-NMR, FT-IR, and mass spectroscopy. The antibacterial activities of the synthesized compounds were screened against standard strains of six Gram positive and four Gram negative bacteria using the microbroth dilution assay. Most of the compounds studied showed promising activities against

  合成了几种新的取代磺酰胺化合物，其结构经 1H-NMR、13C-NMR、FT-IR 和质谱证实。使用微量肉汤稀释测定法针对六种革兰氏阳性菌和四种革兰氏阴性菌的标准菌株筛选合成化合物的抗菌活性。大多数研究的化合物对两种类型的细菌都显示出有希望的活性。
• Design, synthesis, and computational studies of benzimidazole derivatives as new antitubercular agents
  作者：Gozde Yalcin-Ozkat、Ronak H. Ersan、Mahmut Ulger、Seda T. Ulger、Serdar Burmaoglu、Ilkay Yildiz、Oztekin Algul

  DOI：10.1080/07391102.2022.2036241

  日期：——

  tuberculosis has led researchers to new drug targets. The development of new compounds that have effective inhibitory properties with the selective vital structure of Mycobacterium tuberculosis is required in new scientific approaches. The most important of these approaches is the development of inhibitor molecules for Mycobacterium cell wall targets. In this study, first of all, the antitubercular activity

  摘要 结核分枝杆菌耐药菌株的增加促使研究人员寻找新的药物靶点。开发具有有效抑制结核分枝杆菌活性结构的新化合物在新的科学方法中是必需的。这些方法中最重要的是开发针对分枝杆菌细胞壁靶标的抑制剂分子。本研究首先通过实验测定了23种苯并咪唑衍生物的抗结核活性。然后用 4 个不同的靶标进行分子对接研究：阿拉伯糖基转移酶 C (EmbC)、丝状温度敏感突变体 Z (FtsZ)、蛋白酪氨酸磷酸酶 B (PtpB) 和十碳烯基磷酸-β-D-核糖-2'-氧化酶 ( DPRE1). 已确定苯并咪唑衍生物通过 DprE1 酶表现出活性。已知在从阿拉伯半乳聚糖合成细胞包膜中具有重要作用的DprE1在耐药性的形成中也有效。由于这个特点，DprE1 酶已成为药物开发研究的重要目标。此外，它被选为本研究的目标。本研究旨在鉴定抑制 DprE1 的分子，以开发更有效和选择性的抗结核药物。为此，AutoDock Vina 和
• Synthesis and Spectral Properties of the Complexes of Cobalt(II), Nickel(II), Copper(II), Zinc(II), and Cadmium(II) with 2‐(Thiomethyl‐2′‐benzimidazolyl)‐benzimidazole
  作者：S. Satyanarayana、K. R. Nagasundara

  DOI：10.1081/sim-120037514

  日期：2004.5

  Synthesis of 2-(thiomethyl-2'-benzimidazolyl)benzimidazole (L) and its metal complexes of the formulae ML2(ClO4)(2) . xH(2)O (M = Co, x = 3; M = Ni, Zn, or Cd, x = 2; M = Cu, x = 1) and MLBr2 (M = Co, Ni, Cu, Zn, or Cd) are described. They have been characterized by measuring physical properties, IR, NMR, and electronic spectral studies. The electronic spectral and magnetic moment data Suggest an octahedral geometry for the cobalt(H) and nickel(11) perchlorate complexes, a tetrahedral geometry for the cobalt(II) and nickel(II) bromo complexes and a pseudo tetrahedral geometry for the copper(H) perchlorate and copper(H) bromide complexes. Based on elemental analyses, conductivity measurements and IR and NMR spectral Studies, a six-coordinate geometry for cadmium perchlorate complex and various four-coordinate geometries for zinc perchlorate and bromo complexes of cadmium and zinc have been proposed.
• Sarhan, A. A. O.; Hozien, Z. A.; El-Sherief, H. A. H., Polish Journal of Chemistry, 1995, vol. 69, # 11, p. 1479 - 1483
  作者：Sarhan, A. A. O.、Hozien, Z. A.、El-Sherief, H. A. H.、Mahmoud, A. M.

  DOI：——

  日期：——