4-(4-carboxyphenethylamino)-6-nitroquinazoline | 647376-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-(4-carboxyphenethylamino)-6-nitroquinazoline
• 英文别名: 4-{2-[(6-Nitroquinazolin-4-yl)amino]ethyl}benzoic acid；4-[2-[(6-nitroquinazolin-4-yl)amino]ethyl]benzoic acid
• CAS: 647376-17-8
• 化学式: C₁₇H₁₄N₄O₄
• 分子量: 338.323
• InChiKey: WHUXTXXKBYMDBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(4-carboxyphenethylamino)-6-nitroquinazoline 在 ammonium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以91%的产率得到4-[2-(6-Nitro-quinazolin-4-ylamino)-ethyl]-benzamide
  参考文献：
  名称：

  A novel structural class of potent inhibitors of NF-κB activation: structure–activity relationships and biological effects of 6-aminoquinazoline derivatives

  摘要：

  In this study, we have investigated the roles of substituents on the terminal phenyl ring at the C(4)-position of the quinazoline core to complete the structure-activity relationships (SARs) of our NF-kappaB activation inhibitors. Among them, compound 12j afforded highly potent inhibitory activity toward NF-kappaB transcriptional activation with IC50 value of 2nM, along with an excellent in vivo efficacy by reducing the edema formation seen in carrageenin-induced inflammation of the rat hind paw. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00438-3
• 作为产物：
  描述：

  4-氯-6-硝基喹唑啉 在 sodium hydroxide 、 三乙胺 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 2.0h， 生成 4-(4-carboxyphenethylamino)-6-nitroquinazoline
  参考文献：
  名称：

  A novel structural class of potent inhibitors of NF-κB activation: structure–activity relationships and biological effects of 6-aminoquinazoline derivatives

  摘要：

  In this study, we have investigated the roles of substituents on the terminal phenyl ring at the C(4)-position of the quinazoline core to complete the structure-activity relationships (SARs) of our NF-kappaB activation inhibitors. Among them, compound 12j afforded highly potent inhibitory activity toward NF-kappaB transcriptional activation with IC50 value of 2nM, along with an excellent in vivo efficacy by reducing the edema formation seen in carrageenin-induced inflammation of the rat hind paw. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00438-3