N1,N12-bis(1-benzyl-2-butyl-1H-imidazo[4,5-c]quinolin-4-yl)dodecane-1,12-diamine | 1357308-68-9

• 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: N1,N12-bis(1-benzyl-2-butyl-1H-imidazo[4,5-c]quinolin-4-yl)dodecane-1,12-diamine
• 英文别名: N,N'-bis(1-benzyl-2-butylimidazo[4,5-c]quinolin-4-yl)dodecane-1,12-diamine
• CAS: 1357308-68-9
• 化学式: C₅₄H₆₆N₈
• 分子量: 827.172
• InChiKey: UJXVGJFCQHROLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.2
• 重原子数：
  62
• 可旋转键数：
  25
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  85.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,12-二氨基十二烷 、 1-Benzyl-2-butyl-4-chloroimidazo[4,5-c]quinoline 以 甲醇 为溶剂， 生成 N1,N12-bis(1-benzyl-2-butyl-1H-imidazo[4,5-c]quinolin-4-yl)dodecane-1,12-diamine
  参考文献：
  名称：

  Toll-Like Receptor (TLR)-7 and -8 Modulatory Activities of Dimeric Imidazoquinolines

  摘要：

  Toll-like receptors (TLRs) are pattern recognition receptors that recognize specific molecular patterns present in molecules that are broadly shared by pathogens but are structurally distinct from host molecules. The TLR7-agonistic imidazoquinolines are of interest as vaccine adjuvants given their ability to induce pronounced Th1-skewed humoral responses. Minor modifications on the imidazoquinoline scaffold result in TLR7-antagonistic compounds which may be of value in addressing innate immune activation-driven immune exhaustion observed in HIV. We describe the syntheses and evaluation of TLR7 and TLR8 modulatory activities of dimeric constructs of imidazoquinoline linked at the C2, C4, C8, and N-1-aryl positions. Dinners linked at the C4, C8, and N-1-aryl positions were agonistic at TLR7; only the N-1-aryl dimer with a 12-carbon linker was dual TLR7/8 agonistic. Dimers linked at C2 position showed antagonistic activities at TLR7 and TLR8; the C2 dimer with a propylene spacer was maximally antagonistic at both TLR7 and TLR8.

  DOI：

  10.1021/jm2010207

文献信息

• Toll-Like Receptor (TLR)-7 and -8 Modulatory Activities of Dimeric Imidazoquinolines
  作者：Nikunj M. Shukla、Cole A. Mutz、Subbalakshmi S. Malladi、Hemamali J. Warshakoon、Rajalakshmi Balakrishna、Sunil A. David

  DOI：10.1021/jm2010207

  日期：2012.2.9

  Toll-like receptors (TLRs) are pattern recognition receptors that recognize specific molecular patterns present in molecules that are broadly shared by pathogens but are structurally distinct from host molecules. The TLR7-agonistic imidazoquinolines are of interest as vaccine adjuvants given their ability to induce pronounced Th1-skewed humoral responses. Minor modifications on the imidazoquinoline scaffold result in TLR7-antagonistic compounds which may be of value in addressing innate immune activation-driven immune exhaustion observed in HIV. We describe the syntheses and evaluation of TLR7 and TLR8 modulatory activities of dimeric constructs of imidazoquinoline linked at the C2, C4, C8, and N-1-aryl positions. Dinners linked at the C4, C8, and N-1-aryl positions were agonistic at TLR7; only the N-1-aryl dimer with a 12-carbon linker was dual TLR7/8 agonistic. Dimers linked at C2 position showed antagonistic activities at TLR7 and TLR8; the C2 dimer with a propylene spacer was maximally antagonistic at both TLR7 and TLR8.