N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-2,6-difluoro-4-methoxybenzenesulfonamide | 1555544-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-2,6-difluoro-4-methoxybenzenesulfonamide
• 英文别名: N-[4-(4-chloroimidazol-1-yl)-3-methoxy-phenyl]-2-fluoro-4-methoxy-6-(trifluoromethyl)benzenesulfonamide；N-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-2-fluoro-4-methoxy-6-(trifluoromethyl)benzenesulfonamide
• CAS: 1555544-12-1
• 化学式: C₁₈H₁₄ClF₄N₃O₄S
• 分子量: 479.839
• InChiKey: QFIHIGRKMUJUEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  90.8
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-chloro-1-(2-methoxy-4-nitrophenyl)-1H-imidazole 在 4-二甲氨基吡啶 、 氯化铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-2,6-difluoro-4-methoxybenzenesulfonamide
  参考文献：
  名称：

  Synthesis and characterization of new N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)amide/sulfonamide derivatives as possible antimicrobial and antitubercular agents

  摘要：

  In this paper we report the SAR studies of a series of N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)amide and N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)sulfonamide derivatives 6(a-o) and 7(a-o), were synthesized in good yields and characterized by H-1 NMR, C-13 NMR and mass spectral analyses. The preparation of the key intermediate highlights an optimized palladium catalyzed (Pd-2(dba)(3)/RuPhos) Buchwald cross-coupling of intermediate 2 and 3. 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 7d, 7f, 7h and 7n displayed significant activity against Mycobacterium tuberculosis H37Rv strain. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.002