2-[2-(2,4-dichloro-phenyl)-vinyl]-5-nitro-1H-benzimidazole | 27503-62-4

• 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-[2-(2,4-dichloro-phenyl)-vinyl]-5-nitro-1H-benzimidazole
• 英文别名: 2-(2,4-dichloro-styryl)-5-nitro-1(3)H-benzoimidazole；2-[2-(2,4-dichlorophenyl)ethenyl]-6-nitro-1H-benzimidazole
• CAS: 27503-62-4
• 化学式: C₁₅H₉Cl₂N₃O₂
• 分子量: 334.161
• InChiKey: VQONEBSQBNCLEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  反式-2,4-二氯苯乙烯酸 、 4-硝基邻苯二胺 以 乙二醇 为溶剂， 反应 6.0h， 以70.12%的产率得到2-[2-(2,4-dichloro-phenyl)-vinyl]-5-nitro-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.