2-[4-(1H-[1,2,4]-triazol-1-yl) phenyl]-1-(2-methylbenzyl)-4,6-difluoro-1H-benzo[d]imidazole | 1163729-07-4

• 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-[4-(1H-[1,2,4]-triazol-1-yl) phenyl]-1-(2-methylbenzyl)-4,6-difluoro-1H-benzo[d]imidazole
• 英文别名: 4,6-Difluoro-1-(o-tolylmethyl)-2-[4-(1,2,4-triazol-1-yl)phenyl]benzimidazole；4,6-difluoro-1-[(2-methylphenyl)methyl]-2-[4-(1,2,4-triazol-1-yl)phenyl]benzimidazole
• CAS: 1163729-07-4
• 化学式: C₂₃H₁₇F₂N₅
• 分子量: 401.418
• InChiKey: XYYIGZGATLJHPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  48.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-[4-(1H-[1,2,4]-triazol-1-yl)phenyl]-4,6-difluoro-1H-benzo[d]imidazole 、 2-甲基苄溴 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以79%的产率得到2-[4-(1H-[1,2,4]-triazol-1-yl) phenyl]-1-(2-methylbenzyl)-4,6-difluoro-1H-benzo[d]imidazole
  参考文献：
  名称：

  SAR study of clubbed [1,2,4]-triazolyl with fluorobenzimidazoles as antimicrobial and antituberculosis agents

  摘要：

  In the present study, a series of novel 2-[4-(1H-[1,2,4]-triazol-1-yl)phenyl]-1-substituted-4,6-difluoro-1H-benzo[d]imidazole derivatives are synthesized by the alkylation of 2-[4-(1H-[1,2,4]-triazol-1-yl)phenyl]-4,6-difluoro-1H-benzo[d]imidazole with substituted alkyl and aryl halides. The compounds were evaluated for their preliminary in-vitro antibacterial activity against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, and Salmonella typhosa and then were screened for their antitubercular activity against Mycobacterium tuberculosis H37Rv strain by broth microdilution assay method. The antibacterial data suggested that the analogs with electronegative substituents emerged as promising antimicrobials. It was also observed that the promising antimicrobials have proved to be better antimycobacterials. Few of selected analogs are under further evaluation for secondary antitubercular screening, as they have shown better activity compared to rifampin. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.12.001

文献信息

• SAR study of clubbed [1,2,4]-triazolyl with fluorobenzimidazoles as antimicrobial and antituberculosis agents
  作者：Ganesh Rajaram Jadhav、Mohammad Usman Shaikh、Rajesh Prabhakar Kale、Mahendra Ramesh Shiradkar、Charansingh Harnamsingh Gill

  DOI：10.1016/j.ejmech.2008.12.001

  日期：2009.7

  In the present study, a series of novel 2-[4-(1H-[1,2,4]-triazol-1-yl)phenyl]-1-substituted-4,6-difluoro-1H-benzo[d]imidazole derivatives are synthesized by the alkylation of 2-[4-(1H-[1,2,4]-triazol-1-yl)phenyl]-4,6-difluoro-1H-benzo[d]imidazole with substituted alkyl and aryl halides. The compounds were evaluated for their preliminary in-vitro antibacterial activity against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, and Salmonella typhosa and then were screened for their antitubercular activity against Mycobacterium tuberculosis H37Rv strain by broth microdilution assay method. The antibacterial data suggested that the analogs with electronegative substituents emerged as promising antimicrobials. It was also observed that the promising antimicrobials have proved to be better antimycobacterials. Few of selected analogs are under further evaluation for secondary antitubercular screening, as they have shown better activity compared to rifampin. (C) 2009 Elsevier Masson SAS. All rights reserved.