4-(5-bromo-1H-benzo[d]imidazol-2-yl)tetrazolo[1,5-a]quinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(5-bromo-1H-benzo[d]imidazol-2-yl)tetrazolo[1,5-a]quinoline
• 英文别名: 4-(6-bromo-1H-benzimidazol-2-yl)tetrazolo[1,5-a]quinoline
• 化学式: C₁₆H₉BrN₆
• 分子量: 365.192
• InChiKey: APGNDYVIEJEFHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯-3-喹啉甲醛 在 sodium azide 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.07h， 生成 4-(5-bromo-1H-benzo[d]imidazol-2-yl)tetrazolo[1,5-a]quinoline
  参考文献：
  名称：

  Microwave-assisted synthesis of some new tetrazolo[1,5-a]quinoline-based benzimidazoles catalyzed by p-TsOH and investigation of their antimicrobial activity

  摘要：

  Keeping the objective to build up a new structural class of potent antimicrobials, a series of some new 4-Benzimidazol-2-yl tetrazolo[1,5-a]quinoline derivatives has been synthesized by reaction of tetrazolo[1,5-a]quinoline-4-carbaldehyde and o-phenylenediamine in the presence of an organocatalyst p-TsOH under the influence of microwave irradiation. The identity of all the compounds has been established by H-1 NMR, C-13 NMR, FTIR, and elemental analysis. The synthesized compounds were subjected to in vitro antimicrobial screening against a representative panel of pathogenic strains including three Gram-positive bacteria (Bacillus subtilis, Clostridium tetani, and Streptococcus pneumoniae) and three Gram-negative bacteria (Escherichia coli, Salmonella typhi, and Vibrio cholerae) as well as two fungal organisms (Aspergillus fumigatus and Candida albicans) by employing broth microdilution method. Of the compounds studied, compound 5e demonstrated significant activity against a Gram-positive bacteria Bacillus subtilis.

  DOI：

  10.1007/s00044-010-9388-0

文献信息

• Microwave-assisted synthesis of some new tetrazolo[1,5-a]quinoline-based benzimidazoles catalyzed by p-TsOH and investigation of their antimicrobial activity
  作者：Divyesh C. Mungra、Manish P. Patel、Ranjan G. Patel

  DOI：10.1007/s00044-010-9388-0

  日期：2011.7

  Keeping the objective to build up a new structural class of potent antimicrobials, a series of some new 4-Benzimidazol-2-yl tetrazolo[1,5-a]quinoline derivatives has been synthesized by reaction of tetrazolo[1,5-a]quinoline-4-carbaldehyde and o-phenylenediamine in the presence of an organocatalyst p-TsOH under the influence of microwave irradiation. The identity of all the compounds has been established by H-1 NMR, C-13 NMR, FTIR, and elemental analysis. The synthesized compounds were subjected to in vitro antimicrobial screening against a representative panel of pathogenic strains including three Gram-positive bacteria (Bacillus subtilis, Clostridium tetani, and Streptococcus pneumoniae) and three Gram-negative bacteria (Escherichia coli, Salmonella typhi, and Vibrio cholerae) as well as two fungal organisms (Aspergillus fumigatus and Candida albicans) by employing broth microdilution method. Of the compounds studied, compound 5e demonstrated significant activity against a Gram-positive bacteria Bacillus subtilis.