2-(1H-indol-3-yl)-6-nitro-1H-benzo[d]imidazole

• 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-indol-3-yl)-6-nitro-1H-benzo[d]imidazole
• 英文别名: 2-(1h-Indol-3-yl)-5-nitro-1h-benzimidazole；2-(1H-indol-3-yl)-6-nitro-1H-benzimidazole
• 化学式: C₁₅H₁₀N₄O₂
• 分子量: 278.27
• InChiKey: DFGSYXYAZFSUEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-indol-3-yl)-6-nitro-1H-benzo[d]imidazole 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 四丁基溴化铵 、 potassium carbonate 、 sodium ascorbate 作用下， 以 水 、 乙腈 、 叔丁醇 为溶剂， 反应 12.0h， 生成 1-((1H-1, 2, 3-triazol-4-yl)methyl)-2-(1-((1H-1, 2, 3-triazol-4-yl) methyl)-1H-indol-3-yl)-6-nitro-1H-benzo[d]imidazole
  参考文献：
  名称：

  高效[3 + 2]环加成：新型1H-吲哚-3-基苯并[d]咪唑双三唑的点击合成

  摘要：

  一系列新颖的1-（（（1 H -1,2,3-三唑-4-基）甲基）-2-（1-（（1 H -1,2,3-三唑-4-基）甲基） -5-取代-1 H吲哚-3-基-6取代1 H苯并[ d ]咪唑5a – i是用点击化学法制备的，是一种理想的策略，其中[3 + 2]叠氮化物与已开发出末端炔烃作为目标化合物。在路线II中，5个取代基1 H-吲哚3-甲醛1a - c与5个取代基邻苯二胺8反应生成所需的产物，即6个取代基2-（5个取代基1 H-吲哚‐3‐yl）‐1 H‐苯并[ d ]咪唑6a – i。在这里，6a – i与2当量的炔丙基溴7反应，得到新的6取代的2–（5–取代的‐1–（prop‐2‐yn‐1‐基）−1 H‐吲哚‐3‐基）−1 -（prop-2-yn-1-基）-1 H-苯并[ d ]咪唑4a – i。图4a -我用2当量的NaN的反应3中吨丁醇/水（1：2），并添加硫酸铜的催化量的4 ·5H

  DOI：

  10.1002/jhet.3679
• 作为产物：
  描述：

  3-吲哚甲醛 在 sodium metabisulfite 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(1H-indol-3-yl)-6-nitro-1H-benzo[d]imidazole
  参考文献：
  名称：

  Benzimidazole derivatives: synthesis, leishmanicidal effectiveness, and molecular docking studies

  摘要：

  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.

  DOI：

  10.1007/s00044-012-0375-5

文献信息

• Synthesis, Antimicrobial and Antibiofilm Activities, and Molecular Docking Investigations of 2-(1H-Indol-3-yl)-1H-benzo[d]imidazole Derivatives
  作者：Elena Y. Mendogralo、Larisa Y. Nesterova、Ekaterina R. Nasibullina、Roman O. Shcherbakov、Danil A. Myasnikov、Alexander G. Tkachenko、Roman Y. Sidorov、Maxim G. Uchuskin

  DOI：10.3390/molecules28207095

  日期：——

  chemoselective synthesis of 2-(1H-indol-3-yl)-1H-benzo[d]imidazole derivatives is presented. We report on the antimicrobial activity of synthesized 2-(1H-indol-3-yl)-1H-benzo[d]imidazoles with significant activity against Staphylococcus aureus ATCC 25923, Staphylococcus aureus ATCC 43300 (MRSA), Mycobacterium smegmatis (mc(2)155/ATCC 700084), and Candida albicans ATCC 10231. High activity against staphylococci

  由于抗生素耐药性的增加和病原体生物膜的形成，许多细菌和真菌感染的治疗仍然是一个问题。在本文中，提出了化学选择性合成2-(1H-吲哚-3-基)-1H-苯并[d]咪唑衍生物的方法。我们报告了合成的 2-(1H-indol-3-yl)-1H-苯并[d]咪唑的抗菌活性，对金黄色葡萄球菌 ATCC 25923、金黄色葡萄球菌 ATCC 43300 (MRSA)、耻垢分枝杆菌 (mc(2) 具有显着活性。 )155/ATCC 700084) 和白色念珠菌 ATCC 10231。吲哚基苯并[d]咪唑 3ao 和 3aq（最低抑菌浓度 (MIC) < 1 µg/mL）以及 3aa 和 3ad (MIC 3.9–7.8) 对葡萄球菌具有高活性微克/毫升）。2-(1H-吲哚-3-基)-1-甲基-1H-苯并[d]咪唑 (3ag) 对耻垢分枝杆菌和白色念珠菌具有低 MIC（3.9 µg/mL 和 3.9 µg/分
• 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.
• Highly Efficient [3 + 2] Cycloaddition: Click Synthesis of Novel 1 <i>H</i> ‐indol‐3‐yl‐benzo[ <i>d</i> ]imidazole Bis‐triazoles
  作者：Mahesh Goud Bakkolla、Ashok Kumar Taduri、Rama Devi Bhoomireddy

  DOI：10.1002/jhet.3679

  日期：2019.9

  2‐yn‐1‐yl)‐1H‐benzo[d]imidazole 4a–i. 4a–i were reacted with 2 equiv of NaN3 in t‐butanol/water (1:2) and add catalytic amount of CuSO4.5H2O. Stir the reaction mixture at room temperature to get the target products 5a–i. Here, obtained products contain four rings, that is, one indole, two triazoles, and one benzimidazole. The main advantages of this method are short reaction times, easy workup, higher

  一系列新颖的1-（（（1 H -1,2,3-三唑-4-基）甲基）-2-（1-（（1 H -1,2,3-三唑-4-基）甲基） -5-取代-1 H吲哚-3-基-6取代1 H苯并[ d ]咪唑5a – i是用点击化学法制备的，是一种理想的策略，其中[3 + 2]叠氮化物与已开发出末端炔烃作为目标化合物。在路线II中，5个取代基1 H-吲哚3-甲醛1a - c与5个取代基邻苯二胺8反应生成所需的产物，即6个取代基2-（5个取代基1 H-吲哚‐3‐yl）‐1 H‐苯并[ d ]咪唑6a – i。在这里，6a – i与2当量的炔丙基溴7反应，得到新的6取代的2–（5–取代的‐1–（prop‐2‐yn‐1‐基）−1 H‐吲哚‐3‐基）−1 -（prop-2-yn-1-基）-1 H-苯并[ d ]咪唑4a – i。图4a -我用2当量的NaN的反应3中吨丁醇/水（1：2），并添加硫酸铜的催化量的4 ·5H