3-[5-(3-chloro-4-fluorophenylamino)pentyloxy]-1-hydroxy-9H-xanthen-9-one | 1443044-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-[5-(3-chloro-4-fluorophenylamino)pentyloxy]-1-hydroxy-9H-xanthen-9-one
• 英文别名: 3-[5-(3-Chloro-4-fluoroanilino)pentoxy]-1-hydroxyxanthen-9-one；3-[5-(3-chloro-4-fluoroanilino)pentoxy]-1-hydroxyxanthen-9-one
• CAS: 1443044-07-2
• 化学式: C₂₄H₂₁ClFNO₄
• 分子量: 441.886
• InChiKey: PKBZYKJEBSJTLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  水杨酸 在 Eaton′s Reagent 、 potassium carbonate 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 4.58h， 生成 3-[5-(3-chloro-4-fluorophenylamino)pentyloxy]-1-hydroxy-9H-xanthen-9-one
  参考文献：
  名称：

  Design, synthesis, and in vitro antibacterial screening of some novel 3-pentyloxy-1-hydroxyxanthone derivatives

  摘要：

  A series of 3-pentyloxy-1-hydroxyxanthone derivatives were synthesized by four-step reactions: first cyclocondensation between salicylic acid and phloroglucinol in the presence of Eaton's reagents, then alkylation with 1,5-dibromopentane, followed by nucleophilic substitution by different nucleophiles to obtain final compounds. Molecular structures of the synthesized compounds were elucidated by FT-IR, H-1 NMR, C-13 NMR, mass spectral data, and elemental analysis. The in vitro antibacterial activity was evaluated by MIC determination using broth dilution method against representative three Gram-positive and three Gram-negative bacterial strains with reference to ofloxacin. All the synthesized compounds showed antibacterial activity; besides the compounds 7f and 7g showed better Gram-positive and Gram-negative antibacterial activities.

  DOI：

  10.1007/s00044-013-0653-x

文献信息

• Design, synthesis, and in vitro antibacterial screening of some novel 3-pentyloxy-1-hydroxyxanthone derivatives
  作者：Aparoop Das、Md. Mutahar Shaikh、Srabanti Jana

  DOI：10.1007/s00044-013-0653-x

  日期：2014.1

  A series of 3-pentyloxy-1-hydroxyxanthone derivatives were synthesized by four-step reactions: first cyclocondensation between salicylic acid and phloroglucinol in the presence of Eaton's reagents, then alkylation with 1,5-dibromopentane, followed by nucleophilic substitution by different nucleophiles to obtain final compounds. Molecular structures of the synthesized compounds were elucidated by FT-IR, H-1 NMR, C-13 NMR, mass spectral data, and elemental analysis. The in vitro antibacterial activity was evaluated by MIC determination using broth dilution method against representative three Gram-positive and three Gram-negative bacterial strains with reference to ofloxacin. All the synthesized compounds showed antibacterial activity; besides the compounds 7f and 7g showed better Gram-positive and Gram-negative antibacterial activities.