6-(tert-butyl)-N-(4-(tert-butyl)phenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(tert-butyl)-N-(4-(tert-butyl)phenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide
• 英文别名: 6-tert-butyl-N-(4-tert-butylphenyl)-4-oxo-1H-quinoline-3-carboxamide
• 化学式: C₂₄H₂₈N₂O₂
• 分子量: 376.499
• InChiKey: XPNZEICJYVUDFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(tert-butyl)-N-(4-(tert-butyl)phenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以72%的产率得到6-(tert-butyl)-N-(4-(tert-butyl)phenyl)-1-(2-morpholinoethyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation of 4-oxoquinoline-3-carboxamides derivatives as potent anti-fibrosis agents

  摘要：

  Thirty-one 4-oxoquinoline-3-carboxamides derivatives were synthesized and evaluated for their anti-fibrotic activities by the inhibition of TGF-beta 1-induced total collagen accumulation and anti-inflammatory activities by the inhibition of LPS-stimulated TNF-alpha production. Among them, three compounds (10a, 10l and 11g) exhibited potent inhibitory effects on both TGF-beta 1-induced total collagen accumulation and LPS-stimulated TNF-a production. Furthermore, oral administrations of 10l at a dose of 20 mg/kg/day for 4 weeks effectively alleviated lung inflammation and injury, and decreased lung collagen accumulation in bleomycin-induced pulmonary fibrosis model. Histopathological evaluation of lung tissue confirmed 10l as a potential, orally active agent for the treatment of pulmonary fibrosis. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.071
• 作为产物：
  描述：

  4-叔丁基苯胺 在 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 potassium hydroxide 作用下， 以 二苯醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 6-(tert-butyl)-N-(4-(tert-butyl)phenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation of 4-oxoquinoline-3-carboxamides derivatives as potent anti-fibrosis agents

  摘要：

  Thirty-one 4-oxoquinoline-3-carboxamides derivatives were synthesized and evaluated for their anti-fibrotic activities by the inhibition of TGF-beta 1-induced total collagen accumulation and anti-inflammatory activities by the inhibition of LPS-stimulated TNF-alpha production. Among them, three compounds (10a, 10l and 11g) exhibited potent inhibitory effects on both TGF-beta 1-induced total collagen accumulation and LPS-stimulated TNF-a production. Furthermore, oral administrations of 10l at a dose of 20 mg/kg/day for 4 weeks effectively alleviated lung inflammation and injury, and decreased lung collagen accumulation in bleomycin-induced pulmonary fibrosis model. Histopathological evaluation of lung tissue confirmed 10l as a potential, orally active agent for the treatment of pulmonary fibrosis. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.071

文献信息

• Synthesis and biological evaluation of 4-oxoquinoline-3-carboxamides derivatives as potent anti-fibrosis agents
  作者：Jun Zhu、Lin He、Liang Ma、Zhe Wei、Jiqiang He、Zhuang Yang、Yuzhi Pu、Dong Cao、Yuzhe Wu、Mingli Xiang、Aihua Peng、Yuquan Wei、Lijuan Chen

  DOI：10.1016/j.bmcl.2014.10.071

  日期：2014.12

  Thirty-one 4-oxoquinoline-3-carboxamides derivatives were synthesized and evaluated for their anti-fibrotic activities by the inhibition of TGF-beta 1-induced total collagen accumulation and anti-inflammatory activities by the inhibition of LPS-stimulated TNF-alpha production. Among them, three compounds (10a, 10l and 11g) exhibited potent inhibitory effects on both TGF-beta 1-induced total collagen accumulation and LPS-stimulated TNF-a production. Furthermore, oral administrations of 10l at a dose of 20 mg/kg/day for 4 weeks effectively alleviated lung inflammation and injury, and decreased lung collagen accumulation in bleomycin-induced pulmonary fibrosis model. Histopathological evaluation of lung tissue confirmed 10l as a potential, orally active agent for the treatment of pulmonary fibrosis. (C) 2014 Elsevier Ltd. All rights reserved.