9-pentadecylaminoacridine | 1615704-69-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-pentadecylaminoacridine
• 英文别名: N-pentadecylacridin-9-amine
• CAS: 1615704-69-2
• 化学式: C₂₈H₄₀N₂
• 分子量: 404.639
• InChiKey: BMCPKPTVGHACIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-苯基邻氨基苯甲酸 在 三氯氧磷 作用下， 以 苯酚 为溶剂， 反应 1.0h， 生成 9-pentadecylaminoacridine
  参考文献：
  名称：

  Synthesis and evaluation of N-alkyl-9-aminoacridines with antibacterial activity

  摘要：

  A series of 9-alkylaminoacridines were synthesized and evaluated for activity against two strains of methicillin-resistant and one strain of methicillin-sensitive Staphylococcus aureus. Results are presented that show a clear structure activity relationship between the N-alkyl chain length and antibacterial activity with peak MIC99 values of 2-3 mu M for alkyl chains ranging from 10 to 14 carbons in length. Although prior work has linked the function of acridine-based compounds to intercalation and topoisomerase inhibition, the present results show that 9-alkylaminoacridines likely function as amphiphilic membrane-active disruptors potentially in a similar manner as quaternary ammonium antimicrobials. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.037

文献信息

• Synthesis and evaluation of N-alkyl-9-aminoacridines with antibacterial activity
  作者：Adam R. Benoit、Charles Schiaffo、Christine E. Salomon、John R. Goodell、Hiroshi Hiasa、David M. Ferguson

  DOI：10.1016/j.bmcl.2014.05.037

  日期：2014.7

  A series of 9-alkylaminoacridines were synthesized and evaluated for activity against two strains of methicillin-resistant and one strain of methicillin-sensitive Staphylococcus aureus. Results are presented that show a clear structure activity relationship between the N-alkyl chain length and antibacterial activity with peak MIC99 values of 2-3 mu M for alkyl chains ranging from 10 to 14 carbons in length. Although prior work has linked the function of acridine-based compounds to intercalation and topoisomerase inhibition, the present results show that 9-alkylaminoacridines likely function as amphiphilic membrane-active disruptors potentially in a similar manner as quaternary ammonium antimicrobials. (C) 2014 Elsevier Ltd. All rights reserved.