N-[2-(4-chlorophenyl)ethyl]-7-nitroquinazolin-4-amine | 344455-12-5

• 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: N-[2-(4-chlorophenyl)ethyl]-7-nitroquinazolin-4-amine
• CAS: 344455-12-5
• 化学式: C₁₆H₁₃ClN₄O₂
• 分子量: 328.758
• InChiKey: MMFJETZSLDBGFC-UHFFFAOYSA-N

物化性质

• 沸点：
  551.6±50.0 °C(Predicted)
• 密度：
  1.426±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2-(4-chlorophenyl)ethyl]-7-nitroquinazolin-4-amine 在 铁粉 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 以85%的产率得到4-N-[2-(4-chlorophenyl)ethyl]quinazoline-4,7-diamine
  参考文献：
  名称：

  Discovery of quinazolines as a novel structural class of potent inhibitors of NF-κB activation

  摘要：

  We disclose here a new structural class of low-molecular-weight inhibitors of NF-kappaB activation that were designed and synthesized by starting from quinazoline derivative 6a. Structure-activity relationship (SAR) studies based on 6a elucidated the structural requirements essential for the inhibitory activity toward NF-kappaB transcriptional activation, and led to the identification of the 6-amino-4-phenethylaminoquinazoline skeleton as the basic framework. In this series of compounds, 11q, containing the 4-phenoxyphenethyl moiety at the C(4)-position, showed strong inhibitory effects on both NF-kappaB transcriptional activation and TNF-alpha production. Furthermore, 11q exhibited an anti-inflammatory effect on carrageenin-induced paw edema in rats. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00440-6
• 作为产物：
  描述：

  2-氨基-4-硝基苯甲酸 在 盐酸 、 氯化亚砜 、 氨 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 生成 N-[2-(4-chlorophenyl)ethyl]-7-nitroquinazolin-4-amine
  参考文献：
  名称：

  Discovery of quinazolines as a novel structural class of potent inhibitors of NF-κB activation

  摘要：

  We disclose here a new structural class of low-molecular-weight inhibitors of NF-kappaB activation that were designed and synthesized by starting from quinazoline derivative 6a. Structure-activity relationship (SAR) studies based on 6a elucidated the structural requirements essential for the inhibitory activity toward NF-kappaB transcriptional activation, and led to the identification of the 6-amino-4-phenethylaminoquinazoline skeleton as the basic framework. In this series of compounds, 11q, containing the 4-phenoxyphenethyl moiety at the C(4)-position, showed strong inhibitory effects on both NF-kappaB transcriptional activation and TNF-alpha production. Furthermore, 11q exhibited an anti-inflammatory effect on carrageenin-induced paw edema in rats. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00440-6

文献信息

• Structure–activity relationships of quinazoline derivatives: dual-acting compounds with inhibitory activities toward both TNF-α production and T Cell proliferation
  作者：Masanori Tobe、Yoshiaki Isobe、Hideyuki Tomizawa、Mitsuhiro Matsumoto、Fumihiro Obara、Takahiro Nagasaki、Hideya Hayashi

  DOI：10.1016/s0960-894x(00)00718-6

  日期：2001.2

  We synthesized 4-chlorophenethylaminoquinazoline derivatives and evaluated their inhibitory activities toward both TNF-alpha production and T cell proliferation responses; Compound 2f, containing a piperazine ring at the C(7)-position of the quinazoline ring, exhibited more potent inhibitory activities toward both than the lead compound 1a. A smaller N-substituent in the piperazine ring was required for inhibition of TNF-alpha production. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Discovery of quinazolines as a novel structural class of potent inhibitors of NF-κB activation
  作者：Masanori Tobe、Yoshiaki Isobe、Hideyuki Tomizawa、Takahiro Nagasaki、Hirotada Takahashi、Tominaga Fukazawa、Hideya Hayashi

  DOI：10.1016/s0968-0896(02)00440-6

  日期：2003.2

  We disclose here a new structural class of low-molecular-weight inhibitors of NF-kappaB activation that were designed and synthesized by starting from quinazoline derivative 6a. Structure-activity relationship (SAR) studies based on 6a elucidated the structural requirements essential for the inhibitory activity toward NF-kappaB transcriptional activation, and led to the identification of the 6-amino-4-phenethylaminoquinazoline skeleton as the basic framework. In this series of compounds, 11q, containing the 4-phenoxyphenethyl moiety at the C(4)-position, showed strong inhibitory effects on both NF-kappaB transcriptional activation and TNF-alpha production. Furthermore, 11q exhibited an anti-inflammatory effect on carrageenin-induced paw edema in rats. (C) 2002 Elsevier Science Ltd. All rights reserved.