4-(3,4,5-trimethoxyphenyl)amine-6,7,8-trimethoxyquinazoline hydrochloride

• 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-(3,4,5-trimethoxyphenyl)amine-6,7,8-trimethoxyquinazoline hydrochloride
• 英文别名: 6,7,8-trimethoxy-N-(3,4,5-trimethoxyphenyl)quinazolin-4-amine;hydrochloride
• 化学式: C₂₀H₂₃N₃O₆*ClH
• 分子量: 437.88
• InChiKey: AORDWUVOZGCMIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  93.2
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-氨基-3,4,5-三甲氧基苯甲酸 以 乙醇 为溶剂， 反应 3.25h， 生成 4-(3,4,5-trimethoxyphenyl)amine-6,7,8-trimethoxyquinazoline hydrochloride
  参考文献：
  名称：

  The preparation and sar of 4-(anilino), 4-(phenoxy), and 4-(thiophenoxy)-quinazolines: Inhibitors of p56lck and EGF-R tyrosine kinase activity

  摘要：

  We report herein our preliminary results of a SAR study of quinazoline-based inhibitors of p56(lck) and EGF-R tyrosine kinase activity.(1) The most potent inhibitor of p56(lck) identified, RPR-108518A (10), has an IC50 of 0.50 mu M. The 3-chlorophenoxy- and 3-chlorothiophenoxy- derivatives 5 and 6 were also shown to be extremely potent EGF-R inhibitors. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00034-6

文献信息

• Microwave assisted synthesis of novel 6,7,8-trimethoxy<i>N</i>-substituted-4-aminoquinazoline compounds
  作者：Gang Liu、Lin Sun、Chunping Liu、Chunnuan Ji、Quanwu Wen、Songmei Ma

  DOI：10.1002/jhet.5570450320

  日期：2008.5

  convenient reaction of 6,7,8-trimethoxy-4-chloroquinazoline and aryl (or benzyl) amines was achieved under microwave irradiation in isopropyl alcohol, providing a simple method for synthesis of novel 6,7,8-trimethoxy N-substituted-4-aminoquinazoline compounds in good yield in short time. The title compounds were evaluated for their in vitro anti-proliferative activities against PC3 cell by MTT method.

  在异丙醇中微波辐射下，实现了6,7,8-三甲氧基-4-氯喹唑啉与芳基（或苄基）胺的快速，高效，便捷反应，为合成新型6,7,8-三甲氧基提供了简单的方法N-取代的4-氨基喹唑啉化合物在短时间内产率高。通过MTT法评估标题化合物对PC3细胞的体外抗增殖活性。
• Synthesis and biological activity of novel N-substituted 4-amino-6,7,8-trimethoxyquinazoline compounds
  作者：Gang Liu、Chunping Liu、Lin Sun、Rongjun Qu、Hou Chen、Chunnuan Ji

  DOI：10.1007/s10593-007-0196-5

  日期：2007.10
• Synthesis and bioactivities of 6,7,8-trimethoxy-N-aryl-4-aminoquinazoline derivatives
  作者：Gang Liu、De-Yu Hu、Lin-Hong Jin、Bao-An Song、Song Yang、Ping-Shen Liu、Pinaki S. Bhadury、Yao Ma、Hui Luo、Xian Zhou

  DOI：10.1016/j.bmc.2007.07.006

  日期：2007.10

  A series of 4-aminoquinazoline derivatives is prepared by the nucleophilic substitution reaction of 6,7,8-trimethoxy-4-chloroquinazoline and aryl amine. The structures of the compounds are confirmed by elemental analysis, IR, and H-1 NMR spectral data. The compounds are also evaluated for their ability to inhibit tumor cells PC3, A431, Beap-37, and BGC823 by MTT assays. Among them, 6b and 6e are found as potent inhibitors, with IC50 values ranging from 5.8 to 9.8 mu M, in vitro assay. (c) 2007 Elsevier Ltd. All rights reserved.
• The preparation and sar of 4-(anilino), 4-(phenoxy), and 4-(thiophenoxy)-quinazolines: Inhibitors of p56lck and EGF-R tyrosine kinase activity
  作者：Michael R. Myers、Natalie N. Setzer、Alfred.P. Spada、Allison L. Zulli、Chin-Yi J. Hsu、Asher Zilberstein、Susan E. Johnson、Linda E. Hook、Mary V. Jacoski

  DOI：10.1016/s0960-894x(97)00034-6

  日期：1997.2

  We report herein our preliminary results of a SAR study of quinazoline-based inhibitors of p56(lck) and EGF-R tyrosine kinase activity.(1) The most potent inhibitor of p56(lck) identified, RPR-108518A (10), has an IC50 of 0.50 mu M. The 3-chlorophenoxy- and 3-chlorothiophenoxy- derivatives 5 and 6 were also shown to be extremely potent EGF-R inhibitors. (C) 1997, Elsevier Science Ltd.