5-Bromo-2-[(4-nitrophenoxy)methyl]-1-(2-nitrophenyl)sulfonyl-benzimidazole | 1452579-72-4

• 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-[(4-nitrophenoxy)methyl]-1-(2-nitrophenyl)sulfonyl-benzimidazole
• 英文别名: 5-bromo-2-[(4-nitrophenoxy)methyl]-1-(2-nitrophenyl)sulfonylbenzimidazole
• CAS: 1452579-72-4
• 化学式: C₂₀H₁₃BrN₄O₇S
• 分子量: 533.316
• InChiKey: DNZXUIGEHXYHGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-硝基苯氧乙酸 在 四丁基氯化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 生成 5-Bromo-2-[(4-nitrophenoxy)methyl]-1-(2-nitrophenyl)sulfonyl-benzimidazole 、 6-Bromo-2-[(4-nitrophenoxy)methyl]-1-(2-nitrophenyl)sulfonyl-benzimidazole
  参考文献：
  名称：

  Design and synthesis of positional isomers of 5 and 6-bromo-1-[(phenyl)sulfonyl]-2-[(4-nitrophenoxy)methyl]-1H-benzimidazoles as possible antimicrobial and antitubercular agents

  摘要：

  In this Letter, we report the structure activity relationship (SAR) studies on series of positional isomers of 5(6)-bromo-1-[(phenyl)sulfonyl]-2-[(4-nitrophenoxy)methyl]-1H-benzimidazoles derivatives 7(a-j) and 8(a j) synthesized in good yields and characterized by H-1 NMR, C-13 NMR and mass spectral analyses. The crystal structure of 7a was evidenced by X-ray diffraction study. The newly synthesized compounds were evaluated for their in vitro antibacterial activity against Staphylococcus aureus, (Gram-positive), Escherichia coli and Klebsiella pneumoniae (Gram-negative), antifungal activity against Candida albicans, Aspergillus flavus and Rhizopus sp. and antitubercular activity against Mycobacterium tuberculosis H37Rv, Mycobacterium smegmatis, Mycobacterium fortuitum and MDR-TB strains. The synthesized compounds displayed interesting antimicrobial activity. The compounds 7b, 7e and 7h displayed significant activity against Mycobacterium tuberculosis H37Rv strain. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.072

文献信息

• Design and synthesis of positional isomers of 5 and 6-bromo-1-[(phenyl)sulfonyl]-2-[(4-nitrophenoxy)methyl]-1H-benzimidazoles as possible antimicrobial and antitubercular agents
  作者：P. Karuvalam Ranjith、P. Rajeesh、Karickal R. Haridas、Nayak K. Susanta、Tayur N. Guru Row、R. Rishikesan、N. Suchetha Kumari

  DOI：10.1016/j.bmcl.2013.06.072

  日期：2013.9

  In this Letter, we report the structure activity relationship (SAR) studies on series of positional isomers of 5(6)-bromo-1-[(phenyl)sulfonyl]-2-[(4-nitrophenoxy)methyl]-1H-benzimidazoles derivatives 7(a-j) and 8(a j) synthesized in good yields and characterized by H-1 NMR, C-13 NMR and mass spectral analyses. The crystal structure of 7a was evidenced by X-ray diffraction study. The newly synthesized compounds were evaluated for their in vitro antibacterial activity against Staphylococcus aureus, (Gram-positive), Escherichia coli and Klebsiella pneumoniae (Gram-negative), antifungal activity against Candida albicans, Aspergillus flavus and Rhizopus sp. and antitubercular activity against Mycobacterium tuberculosis H37Rv, Mycobacterium smegmatis, Mycobacterium fortuitum and MDR-TB strains. The synthesized compounds displayed interesting antimicrobial activity. The compounds 7b, 7e and 7h displayed significant activity against Mycobacterium tuberculosis H37Rv strain. (C) 2013 Elsevier Ltd. All rights reserved.