2-(2-hydroxypropyl)furo[2,3-c]quinoline 5-oxide | 1449680-04-9

• 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: 2-(2-hydroxypropyl)furo[2,3-c]quinoline 5-oxide
• CAS: 1449680-04-9
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: IDYIALIFQJUWGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  60.31
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxypropyl)furo[2,3-c]quinoline 5-oxide 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-(4-aminofuro[2,3-c]quinolin-2-yl)propan-2-ol
  参考文献：
  名称：

  Exquisite Selectivity for Human Toll-Like Receptor 8 in Substituted Furo[2,3-c]quinolines

  摘要：

  Toll-like receptor (TLR)-8 agonists activate adaptive immune responses by inducing robust production of T helper 1-polarizing cytokines, suggesting that TLR8-active compounds may be promising candidate adjuvants. We synthesized and evaluated hitherto unexplored furo[2,3-d]quinolines and regioisomeric furo[3,2-c]quinolines derived via a tandem, one-pot Sonogashira coupling and intramolecular 5-endo-dig cyclization strategy in a panel of primary screens. We observed a pure TLR8-agonistic activity profile in select furo[2,3-c]quinolines, with maximal potency conferred by a C2-butyl group (EC50 = 1.6 mu M); shorter, longer, or substituted homologues as well as compounds bearing C1 substitutions were inactive, which was rationalized by docking studies using the recently described crystal structure of human TLR8. The best-in-class compound displayed,prominent proinflammatory cytokine induction (including interleukin-12 and interleukin-18), but was bereft of interferon-alpha inducing properties, confirming its high selectivity for human TLR8.

  DOI：

  10.1021/jm400694d
• 作为产物：
  描述：

  1-(furo[2,3-c]quinolin-2-yl)propan-2-ol 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以81%的产率得到2-(2-hydroxypropyl)furo[2,3-c]quinoline 5-oxide
  参考文献：
  名称：

  Exquisite Selectivity for Human Toll-Like Receptor 8 in Substituted Furo[2,3-c]quinolines

  摘要：

  Toll-like receptor (TLR)-8 agonists activate adaptive immune responses by inducing robust production of T helper 1-polarizing cytokines, suggesting that TLR8-active compounds may be promising candidate adjuvants. We synthesized and evaluated hitherto unexplored furo[2,3-d]quinolines and regioisomeric furo[3,2-c]quinolines derived via a tandem, one-pot Sonogashira coupling and intramolecular 5-endo-dig cyclization strategy in a panel of primary screens. We observed a pure TLR8-agonistic activity profile in select furo[2,3-c]quinolines, with maximal potency conferred by a C2-butyl group (EC50 = 1.6 mu M); shorter, longer, or substituted homologues as well as compounds bearing C1 substitutions were inactive, which was rationalized by docking studies using the recently described crystal structure of human TLR8. The best-in-class compound displayed,prominent proinflammatory cytokine induction (including interleukin-12 and interleukin-18), but was bereft of interferon-alpha inducing properties, confirming its high selectivity for human TLR8.

  DOI：

  10.1021/jm400694d