3-((4,5-dihydro-1H-imidazol-2-yl)methyl)-5-fluoro-1H-indole | 33513-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-((4,5-dihydro-1H-imidazol-2-yl)methyl)-5-fluoro-1H-indole
• 英文别名: 3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-5-fluoro-indole；3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-5-fluoro-1H-indole
• CAS: 33513-85-8
• 化学式: C₁₂H₁₂FN₃
• 分子量: 217.246
• InChiKey: XHSRLGSARCKUQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氟吲哚-3-乙腈 、 乙二胺 在 sulfur 作用下， 以57%的产率得到3-((4,5-dihydro-1H-imidazol-2-yl)methyl)-5-fluoro-1H-indole
  参考文献：
  名称：

  Synthesis, antimicrobial activity, and molecular docking study of fluorine-substituted indole-based imidazolines

  摘要：

  A series of 2- or 3-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole derivatives were synthesized, characterized, and evaluated for their in vitro antibacterial and antifungal activities. Additionally, the synthesized compounds were docked into the II DNA gyrase B active site, and their predicted binding modes were inspected. Inhibitory activity were tested against two species of Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), two species of Gram-positive bacteria (Staphylococcus aureus, Listeria monocytogenes) and two fungi (Candida albicans, Aspergillus niger) using the broth microdilution method. The fluorine-substituted 2-(2-imidazolyl)indole 2b was found to be the most potent antibacterial compound against E. coli and S. aureus strains (MIC value 80 mu g/mL). Compounds showed better activity against Gram-positive bacteria compared to Gram-negative bacteria. The docking results predicted that the imidazoline-indole hybrid moiety bind to the active site protein ATP-binding pocket from E. coli and S. aureus with good interaction energy scores. The significant loss of antibacterial activity for some imidazoline-indole analogs could be attributed to several nonoptimal enzyme interactions, including poor hydrogen bonds provided by Asp73 (E. coli gyrase numbering) or Asp81 (S. aureus gyrase numbering) and an associated water molecule.

  DOI：

  10.1007/s00044-018-2177-x