2-(3’,4’-methylenedioxyphenyl)-5-methoxy-1-H-benzimidazole | 1432753-37-1

• 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: 2-(3’,4’-methylenedioxyphenyl)-5-methoxy-1-H-benzimidazole
• 英文别名: 2-(1,3-benzodioxol-5-yl)-5-methoxy-1H-benzimidazole；2-(1,3-benzodioxol-5-yl)-6-methoxy-1H-benzimidazole
• CAS: 1432753-37-1
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: DNABMCOUCWSDKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  56.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-氯-3,5-二硝基三氟甲苯 、 2-(3’,4’-methylenedioxyphenyl)-5-methoxy-1-H-benzimidazole 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以29%的产率得到2-(benzo[d][1,3]dioxol-5-yl)-1-(2,6-dinitro-4-(trifluoromethyl)phenyl)-5-methoxy-1H-benzo[d]imidazole
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modeling of 1H-benzo[d]imidazole derivatives as novel anti-tubulin polymerization agents

  摘要：

  一系列新化合物（8a–21b）是基于2-苯基-1H-苯并[d]咪唑设计并合成的。化合物18b表现出最强的体外生长抑制活性和显著的微管聚合抑制活性。

  DOI：

  10.1039/c5ra13746b
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 在 sodium metabisulfite 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.0h， 生成 2-(3’,4’-methylenedioxyphenyl)-5-methoxy-1-H-benzimidazole
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modeling of 1H-benzo[d]imidazole derivatives as novel anti-tubulin polymerization agents

  摘要：

  一系列新化合物（8a–21b）是基于2-苯基-1H-苯并[d]咪唑设计并合成的。化合物18b表现出最强的体外生长抑制活性和显著的微管聚合抑制活性。

  DOI：

  10.1039/c5ra13746b

文献信息

• A simple and straightforward synthesis of substituted 2-arylbenzimidazoles over silica gel
  作者：Amit K. Chaturvedi、Arvind S. Negi、Puja Khare

  DOI：10.1039/c3ra22435j

  日期：——

  A solid phase strategy for the synthesis of substituted 2-arylbenzimidazoles over silica gel has been achieved starting from their corresponding o-phenylenediamines 1 and aromatic aldehydes 2. The reaction is very simple, convenient and straightforward, and the products are obtained in moderate to high yields (49–91%).

  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。
• 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.