6-Amino-4-(3-chloro-4-fluoro-phenylamino)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile | 919482-10-3

• 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: 6-Amino-4-(3-chloro-4-fluoro-phenylamino)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile
• CAS: 919482-10-3
• 化学式: C₁₆H₁₀ClFN₄O
• 分子量: 328.733
• InChiKey: FRVPMTQCPFWDOP-UHFFFAOYSA-N

物化性质

• 沸点：
  568.3±50.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.7
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-咪唑甲醛 、 6-Amino-4-(3-chloro-4-fluoro-phenylamino)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 以30%的产率得到4-[(3-chloro-4-fluorophenyl)amino]-6-[(1H-imidazol-5-ylmethyl)amino]-2-oxo-1,2-dihydroquinoline-3-carbonitrile
  参考文献：
  名称：

  Inhibition of Tpl2 kinase and TNFα production with quinoline-3-carbonitriles for the treatment of rheumatoid arthritis

  摘要：

  The synthesis and structure-activity studies of a series of quinoline-3-carbonitriles as inhibitors of Tpl2 kinase are described. Potent inhibitors of Tpl2 kinase with selectivity against a panel of selected kinases in enzymatic assays and specificity in cell-based phosphorylation assays in LPS-treated human monocytes were identified. Selected inhibitors with moderate activity in human whole blood assay effectively inhibited LPS/D-Gal induced TNFalpha release when administered intraperitoneally in mice.

  DOI：

  10.1016/j.bmcl.2006.08.102
• 作为产物：
  描述：

  3-cyano-2,4-dihydroxy-6-nitroquinoline 在 苄基三乙基氯化铵 、 铁粉 、 氯化铵 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 16.17h， 生成 6-Amino-4-(3-chloro-4-fluoro-phenylamino)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile
  参考文献：
  名称：

  Inhibition of Tpl2 kinase and TNFα production with quinoline-3-carbonitriles for the treatment of rheumatoid arthritis

  摘要：

  The synthesis and structure-activity studies of a series of quinoline-3-carbonitriles as inhibitors of Tpl2 kinase are described. Potent inhibitors of Tpl2 kinase with selectivity against a panel of selected kinases in enzymatic assays and specificity in cell-based phosphorylation assays in LPS-treated human monocytes were identified. Selected inhibitors with moderate activity in human whole blood assay effectively inhibited LPS/D-Gal induced TNFalpha release when administered intraperitoneally in mice.

  DOI：

  10.1016/j.bmcl.2006.08.102