5-methoxy,1-(3’,4’-methylenedioxybenzyl)-2-(3”,4”-methylenedioxyphenyl)-1-H-benzimidazole | 1432753-40-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-methoxy,1-(3’,4’-methylenedioxybenzyl)-2-(3”,4”-methylenedioxyphenyl)-1-H-benzimidazole
• 英文别名: 2-(1,3-Benzodioxol-5-yl)-1-(1,3-benzodioxol-5-ylmethyl)-5-methoxybenzimidazole
• CAS: 1432753-40-6
• 化学式: C₂₃H₁₈N₂O₅
• 分子量: 402.406
• InChiKey: WKZRCXZKIMKIMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  胡椒醛 、 4-甲氧基邻苯二胺 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 以49%的产率得到2-(3’,4’-methylenedioxyphenyl)-5-methoxy-1-H-benzimidazole
  参考文献：
  名称：

  在硅胶上简单直接地合成取代的2-芳基苯并咪唑†

  摘要：

  用固相策略合成取代的2-芳基苯并咪唑 硅石从它们相应的邻苯二胺1和芳香醛2开始已经获得了凝胶。该反应非常简单，方便和直接，并且以中等至高收率（49–91％）获得了产物。

  DOI：

  10.1039/c3ra22435j

文献信息

• Nitroarenes as versatile building blocks for the synthesis of unsymmetrical urea derivatives and N-Arylmethyl-2-substituted benzimidazoles
  作者：Paula A. Rodríguez-Huerto、Diana Peña-Solórzano、Cristian Ochoa-Puentes

  DOI：10.1007/s11696-021-01785-7

  日期：2021.12

  contribution, a fast and simple method for the synthesis of unsymmetrical urea derivatives and N-arylmethyl-2-substituted benzimidazoles was developed starting from nitroarenes. The reaction of nitroarenes and phenyl isocyanate or phenyl isothiocyanate in tin (II) chloride dihydrate/choline chloride eutectic mixture afforded the expected urea and thiourea derivatives, while the reaction of different aldehydes

  在这项贡献中，从硝基芳烃开始，开发了一种用于合成不对称脲衍生物和 N-芳甲基-2-取代苯并咪唑的快速简单的方法。硝基芳烃与异氰酸苯酯或异硫氰酸苯酯在二水合氯化锡 (II)/氯化胆碱低共熔混合物中的反应提供了预期的脲和硫脲衍生物，而不同醛与邻硝基苯胺或 4-甲氧基-2-硝基苯胺的反应显示出与 2-取代的类似物相比，获得 N-芳基甲基-2-取代的苯并咪唑具有显着的高偏好。该方法提供了一种直接的替代方法，可以通过操作简单的实验装置以短的反应时间以良好至优异的收率获得目标化合物。一系列不对称的脲和硫脲衍生物以及1，
• A novel synthesis of 2-arylbenzimidazoles in molecular sieves-MeOH system and their antitubercular activity
  作者：Amit K. Chaturvedi、Amit Kumar Verma、Jay Prakash Thakur、Sudeep Roy、Shashi Bhushan Tripathi、Balagani Sathish Kumar、Sadiya Khwaja、Naresh K. Sachan、Ashok Sharma、Debabrata Chanda、Karuna Shanker、Dharmendra Saikia、Arvind S. Negi

  DOI：10.1016/j.bmc.2018.07.049

  日期：2018.8

  Arylbenzimidazoles have been synthesized as antimycobacterial agents. An efficient synthesis has been developed for 2-arylbenzimidazoles from o-phenylenediamines and aromatic aldehydes in molecular sieves-methanol system. The methodology is straightforward to get 2-arylbenzimidazoles (3a-3z) in excellent yields with high chemoselectivity over 2-aryl-1-benzylbenzimidazoles (4a-4z). All these benzimidazole analogues were evaluated against M. tuberculosis in BACTEC radiometric assay. The compounds 4y and 4z exhibited potential antitubercular activity against M. tuberculosis H (37)Rv, MIC at 16 mu M and 24 mu M respectively. The best compound of the series i.e. compound 4y was well tolerated by Swiss-albino mice in acute oral toxicity. Compound 4y possessing a diarylbenzimidazole core, can further be optimized for better activity.