5-bromo-2-[2-(3,4-dimethoxy-phenyl)-vinyl]-1H-benzimidazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-bromo-2-[2-(3,4-dimethoxy-phenyl)-vinyl]-1H-benzimidazole
• 英文别名: 6-bromo-2-[2-(3,4-dimethoxyphenyl)ethenyl]-1H-benzimidazole
• 化学式: C₁₇H₁₅BrN₂O₂
• 分子量: 359.222
• InChiKey: UZDJLLPGXBHNLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.14
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基肉桂酸 、 4-溴邻苯二胺 以 乙二醇 为溶剂， 反应 6.0h， 以79.35%的产率得到5-bromo-2-[2-(3,4-dimethoxy-phenyl)-vinyl]-1H-benzimidazole
  参考文献：
  名称：

  Synthesis and evaluation of in vitro anti-microbial and anti-tubercular activity of 2-styryl benzimidazoles

  摘要：

  A new series of novel 5-(nitro/bromo)-styryl-2-benzimidazoles (1-12) has been synthesized by simple, mild and efficient synthetic protocol by attempted condensation of 5-(nitro/bromo)-o-phenylenediamine with trans-cinnamic acids in ethylene glycol. Screening for in vitro anti-tubercular activity against Mycobacterium tuberculosis H-37 Rv, anti-bacterial activity against Staphylococcus aureus, Escherichia coli, Enterococcus faecalis, Klebsiella pneumoniae bacterial strains and anti-fungal activity against Candida albicans and Asperigillus fumigatus fungal strains were carried out. Compounds 5, 7, 8, 9, 11 showed higher anti-tubercular activity and compounds 7, 8, 10, 11, 12 have proved to be effective with MIC (mu g/ml) and emerged as lead molecules showing excellent activities against a panel of microorganisms. All synthesized compounds were characterized using IR, H-1, C-13 NMR, GC-MS and elemental analysis. (c) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.05.021

文献信息

• Synthesis and evaluation of in vitro anti-microbial and anti-tubercular activity of 2-styryl benzimidazoles
  作者：Ramya V. Shingalapur、Kallappa M. Hosamani、Rangappa S. Keri

  DOI：10.1016/j.ejmech.2009.05.021

  日期：2009.10

  A new series of novel 5-(nitro/bromo)-styryl-2-benzimidazoles (1-12) has been synthesized by simple, mild and efficient synthetic protocol by attempted condensation of 5-(nitro/bromo)-o-phenylenediamine with trans-cinnamic acids in ethylene glycol. Screening for in vitro anti-tubercular activity against Mycobacterium tuberculosis H-37 Rv, anti-bacterial activity against Staphylococcus aureus, Escherichia coli, Enterococcus faecalis, Klebsiella pneumoniae bacterial strains and anti-fungal activity against Candida albicans and Asperigillus fumigatus fungal strains were carried out. Compounds 5, 7, 8, 9, 11 showed higher anti-tubercular activity and compounds 7, 8, 10, 11, 12 have proved to be effective with MIC (mu g/ml) and emerged as lead molecules showing excellent activities against a panel of microorganisms. All synthesized compounds were characterized using IR, H-1, C-13 NMR, GC-MS and elemental analysis. (c) 2009 Elsevier Masson SAS. All rights reserved.